Propanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]- synthesis

8synthesis methods

Product Name:Propanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-
CAS Number:120821-20-7
Molecular formula:C9H20O3Si
Molecular Weight:204.34

89922-82-7 Synthesis

3-[(TERT-BUTYLDIMETHYLSILYL)OXY]-1-PROPANAL

89922-82-7
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Propanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

120821-20-7
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Yield:120821-20-7 431 mg

Reaction Conditions:

with sodium chlorite;sodium dihydrogenphosphate;2-methyl-but-2-ene in water;tert-butyl alcohol; for 1 h;

Steps:

3.2.2. 1-(Bis(2,2,2-trifluoroethyl)phosphoryl)-4-(tert-butyldimethylsilyloxy)butan-2-one (6)

To a solution of 1,3-propanediol (3 mL, 40 mmol) in THF (60 mL) was added NaH (1.2 g, 60%, 20 mmol) at rt. After stirring for 2.5 h, TBSCl (630 mg, 4.3 mmol) was added and the mixture was stirred overnight before the addition of NaHCO₃ solution in MeOH. The solution was then extracted with DCM, washed with water and brine, dried over Na₂SO₄, filtered, concentrated and purified by flash chromatography (30% EtOAc in hexanes) to afford 2-((tert-butyldimethylsilyl)oxy)ethanol ether (800 mg, 90% based on TBSCl) as a colorless oil. To a solution of this TBS ether (590 mg, 3.11 mmol) in DCM (29 mL) was added NaHCO₃ and Dess-Martin periodinane at rt. After stirring for 30 min, the solution was concentrated, diluted with hexane to participate byproduct, filtered and concentrated carefully to give crude 2-((tert-butyldimethylsilyl)oxy)acetaldehyde. A solution of this crude aldehyde in t-BuOH (13 mL) and 2-methyl-2-butene (1.5 mL) was treated with a solution of NaClO₂ (500 mg, 5.5 mmol) and NaH₂PO₄ (1.85 g, 15.4 mmol) in water (12 mL) dropwise. After stirring for 1 h, the reaction was partitioned between brine and DCM. The organic layer was dried over Na₂SO₄, filtered, concentrated and purified by flash chromatography (30% EtOAc in hexanes) to afford acid 11 (431 mg, 68% over 2 steps) as a colorless oil. ¹H NMR (500 MHz, CDCl₃) δ 3.91 (2H, t, J = 6.1 Hz), 2.58 (2H, t, J = 6.1 Hz), 0.89 (9H, s), 0.09 (6H, s).

References:

Qi, Jun;Blanden, Adam R.;Bane, Susan;Kingston, David G.I. [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 17,p. 5247 - 5254] Location in patent:experimental part