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

HRID 618843Notes

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-efe38f46ec7e469d9ba46840afbe35ed
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05955610

Reaction notes

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