(TETRAHYDRO-PYRAN-3-YL)-METHANOL synthesis
- Product Name:(TETRAHYDRO-PYRAN-3-YL)-METHANOL
- CAS Number:14774-36-8
- Molecular formula:C6H12O2
- Molecular Weight:116.16
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Yield: 91%
Reaction Conditions:
with sodium tetrahydroborate in methanol;dichloromethane at -10 - 20; for 4 h;
Steps:
15 Intermediate 15.1 : (tetrahydro-2H-pyran-3-yl)methanol
[00174] At -5 °C-10 °C, to a solution of tetrahydro-2H-pyran-3-carbaldehyde (450 mg, 3.943 mmol) in the co-solvent of DCM/MeOH(6 mL, 15:1 ) was added NaBH4 (90 mg, 2.366 mmol) in several portions. The mixture was stirred at rt for 4 h. Then at 0 °C, to the mixture was added 1 N HCI aq. until no bubble appeared. The mixture was extracted with DCM for 3 times. The organic layer was combined, dried over anhydrous Na2S04, filtered and concentrated to give the title ccompound (416 mg, 91 %) as colorless oil. 1H NMR (300 MHz, DMSO-c/6) δ ppm 4.05 - 3.57 (m, 2H), 3.45 - 3.22 (m, 4H), 3.17 (t, 1 H), 1 .89 - 1 .43 (m, 4H), 1 .37 - 1 .08 (m, 1 H). LC-MS: [M+H]+ = 117.0.
References:
NOVARTIS AG;HE, Feng;DU-CUNY, Lei;XIAO, Qitao;XUN, Guoliang;ZHENG, Qiangang WO2017/149463, 2017, A1 Location in patent:Paragraph 00174
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14774-36-8
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14774-36-8
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