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(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane) synthesis
- Product Name:(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane)
- CAS Number:139356-38-0
- Molecular formula:C20H41ClO2Si2
- Molecular Weight:405.1624
![2-((3R,5R)-3,5-bis(tert-butyldiMethylsilyloxy)cyclohexylidene)ethanol](/CAS/GIF/139356-37-9.gif)
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![(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane)](/CAS/20180601/GIF/139356-38-0.gif)
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Yield:139356-38-0 90%
Reaction Conditions:
with pyridine;bis(trichloromethyl) carbonate in Hexachlorobutadiene at 0 - 20;
Steps:
((1R,3R)-5-(2-Chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) (16)
A solution of pyridine (7.35 g, 93 mmol) in hexane (50 mL) was added over 30 min to a cold solution of compound 15 (18 g, 46.5 mmol) and triphosgene (6.88 g, 23.27 mmol) in hexane at 0 °C. After stirring at 0 °C for 30 min, and then warmed to room temperature and stirred for another 30 min. The reaction mixture was washed with aqueous solution of CuSO4.5H2O. The aqueous solution was extracted with hexane. The combined organic layer were dried over Na2SO4 and concentrated under reduced pressure to afford compound 16 (17 g, 90%), which was used in the next step without any purification. 1H NMR (400 MHz, CDCl3) δ H NMR, 5.52-5.48 (t, 1H, J = 16, 8 Hz), 4.12-4.03 (m, 4H), 2.37-2.27 (m, 2H), 2.24-2.14 (m, 1H), 2.10-2.05 (m, 1H), 1.83-1.78 (m, 1H), 1.74-1.70 (m, 1H), 0.89 (s, 18H), 0.06 (s, 12H); LC-MS (ES+) m/z 405.4 (M+H).
References:
Samala, Ramakrishna;Sharma, Somesh;Basu, Manas K.;Mukkanti;Porstmann, Frank [Tetrahedron Letters,2016,vol. 57,# 12,p. 1309 - 1312] Location in patent:supporting information
![(3S,5S)-3,5-bis(tert-butyldimethylsilyloxy)cyclohexanone](/CAS/20180703/GIF/139356-35-7.gif)
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![(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane)](/CAS/20180601/GIF/139356-38-0.gif)
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![(3S,5S)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1-hydroxy-cyclohexaneMethanol](/CAS/GIF/139356-34-6.gif)
139356-34-6
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$174.90/5mg
![(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane)](/CAS/20180601/GIF/139356-38-0.gif)
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![(3R-trans)-[3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]cyclohexylidene]-acetic Acid Ethyl Ester](/CAS/GIF/139356-36-8.gif)
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![(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane)](/CAS/20180601/GIF/139356-38-0.gif)
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