Tetrahydro-2H-pyran-4-carboxylic acid benzyl ester synthesis
- Product Name:Tetrahydro-2H-pyran-4-carboxylic acid benzyl ester
- CAS Number:871022-58-1
- Molecular formula:C13H16O3
- Molecular Weight:220.26
40191-32-0
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100-51-6
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871022-58-1
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Yield:871022-58-1 1.83 g
Reaction Conditions:
with triethylamine in dichloromethane at 20; for 1 h;Cooling with ice;
Steps:
A
A mixture of tetrahydro-2H-pyran-4-carboxylic acid (1.36 g, 10.45 mmol) and thionyl chloride (7.63 mL, 105 mmol) was heated to gentle reflux for 2.5 h. The mixture was then cooled to room temperature and evaporated in vacuo. To a solution of this tetrahydro-2H-pyran-4-carbonyl chloride in DCM (15 mL) was added Et3N (4.36 mL, 31.4 mmol) and benzyl alcohol (1.622 mL, 15.68 mmol) dropwise while cooled with an ice bath. The formed solurry was stirred with cooling for 30 min, and then at rt 30 min. The mixture was then washed in turn with water, 5% citric acid and saturated aqueous sodium chloride solution. The organic solution was dried over MgS04, and then, concentrated under reduced pressure. The resulting residue was purified by column chromatography (5% to 30% EtOAc-hexane) to give Cap W-22 Step A (1.83 g) as colorless oil.XH NMR (500MHz, CDC13) δ 7.52 - 7.31 (m, 5H), 5.16 (s, 2H), 3.99 (dt, J=l 1.5, 3.6 Hz, 2H), 3.45 (td, J=11.2, 2.9 Hz, 2H), 2.69 - 2.49 (m, 1H), 2.03 - 1.73 (m, 4H).
References:
WO2015/5901,2015,A1 Location in patent:Page/Page column 609; 610
5337-03-1
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871022-58-1
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$281.00/1g