Tetrabutylammonium Fluoride → Trans 2-(Diethyloxyphosphinoylmethyl)-5-(Hydroxymethyl)-1,3-Oxathiolane

HRID 481730Notes

Reaction equation

HRID 481730 reaction equation
[Si]([O:18][CH2:19][C@@H:20]1[O:24][C@@H:23]([CH2:25][P:26]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:27])[S:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:29]([O:28][P:26]([CH2:25][C@H:23]1[S:22][CH2:21][C@H:20]([CH2:19][OH:18])[O:24]1)([O:31][CH2:32][CH3:33])=[O:27])[CH3:30]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131720788Trans 5-(t-Butyldiphenylsilyloxymethyl)-2-(Diethyloxyphosphinoylmethyl)-1,3-Oxathiolane

Product 1

HCID 86752994Trans 2-(Diethyloxyphosphinoylmethyl)-5-(Hydroxymethyl)-1,3-OxathiolaneYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cis and trans 5-(t-butyldiphenylsilyloxy methyl)-2-(diethyloxyphosphinoylmethyl)-1,3-oxathiolane (example 129) (15.68 g, 31.83 mmol) in THF (280 mL) was added tetrabutylammoniumfluoride (1M solution in THF) (38.2 mL, 38.19 mmol, 1.2 eq.) at 0° C. The mixture was stirred at room temperature for 30 min. after which it was evaporated under reduced pressure. The residue was purified by flash chromatography with ethyl acetate: MeOH (95:5 to 93:7) to give 7.39 g of the compound in a 86% yield.

Workup

  1. customwas evaporated under reduced pressure
  2. customThe residue was purified by flash chromatography with ethyl acetate: MeOH (95:5 to 93:7)

Sources & evidence

ORD record
ord-0f81952d7e7b4e1dabcd77cbb5e977b6
Source dataset
uspto-grants-1998_08
Patent number
US05789394

Reaction notes

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