Triethylamine → methanesulfonic acid Trans-2-benzhydryl-tetrahydropyran-4-yl ester

HRID 909706Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([C@H:19]1[CH2:24][C@H:23]([OH:25])[CH2:22][CH2:21][O:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:6]([C@H:19]1[CH2:24][C@H:23]([O:25][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:22][CH2:21][O:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonyl chloride (0.62 g, 5.41 mmol) in dry methylene chloride (10 ml) was added dropwise to a mixture of trans-2-diphenylmethyl-4-hydroxypyran 3a (0.73 g, 2.70 mmol), triethylamine (0.41 g, 4.06 mmol) in methylene chloride (10 ml) and was cooled to 0° C. After one hour, the reaction was gradually allowed to reach room temperature over a period of four hours. Additional methylene chloride (20 ml) was added to the reaction mixture, and the mixture was washed in turn with saturated aqueous sodium bicarbonate, brine and water, then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and purification by flash chromatography gave compound 4a (0.93 g, 99.9% yield) as an oil.

Workup

waitto reach room temperature over a period of four hours
washthe mixture was washed in turn with saturated aqueous sodium bicarbonate, brine and water
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed under reduced pressure, and purification by flash chromatography

Sources & evidence

ORD record: ord-4130444d909340b4a299ef5fa2bcd130
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017791B2

Reaction notes

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