trans-4-(t-Butyldimethylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-dithiolane → Trans 2-(Diethyloxyphosphinoyl)-4-Hydroxymethyl-1,3-Dithiolane

HRID 365778Notes

Reaction equation

[Si]([O:8][CH2:9][C@@H:10]1[CH2:14][S:13][C@@H:12]([P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])[S:11]1)(C(C)(C)C)(C)C>CO.C(Cl)(=O)C.[Cl-].[NH4+]>[CH2:18]([O:17][P:15]([O:20][CH2:21][CH3:22])([C@H:12]1[S:11][C@H:10]([CH2:9][OH:8])[CH2:14][S:13]1)=[O:16])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of trans-4-(t-butyldimethylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-dithiolane (example 49) (9.84 g, 25.46 mmol) in anhydrous methanol (150 mL) was added acetyl chloride (12 drops) at 0° C. The solution was stirred at 0° C. for 30 min and then at room temperature for 3.5 hrs. A saturated solution of ammonium chloride (5 drops) was added and the solution was stirred for 15 min followed by evaporation of the solvents. The crude material was purified by flash chromatography with a mixture of dichloromethane and methanol (94:6) to give a white solid (5.97 g) in 86% yield.

Workup

waitat room temperature for 3.5 hrs
stirringthe solution was stirred for 15 min
customfollowed by evaporation of the solvents
customThe crude material was purified by flash chromatography with a mixture of dichloromethane and methanol (94:6)

Sources & evidence

ORD record: ord-85018eaedb81478f8d3570187284f89c
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127540

Reaction notes

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