Acetic Acid → Acetic acid 3-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl ester

HRID 1893158Notes

Reaction equation

HRID 1893158 reaction equation
[CH2:1]([O:8][CH:9]1[CH:16]2[CH:12]([O:13][C:14]([CH3:18])(C)[O:15]2)[O:11][C:10]1([CH2:21][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])(C1C=CC=CC=1)C1C=CC=CC=1)[CH:19]=[CH2:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:43][C:44](=[O:46])[CH3:45])(=O)C.OS(O)(=O)=O.[C:52](O)(=O)[CH3:53]>>[C:44]([O:43][CH:16]1[CH:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]([C:21]([C:53]2[CH:52]=[CH:19][CH:10]=[CH:9][CH:16]=2)([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:22][SiH2:23][C:36]([CH3:37])([CH3:39])[CH3:38])([CH:19]=[CH2:20])[O:11][CH:12]1[O:13][C:14](=[O:15])[CH3:18])(=[O:46])[CH3:45]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 67360139(6-Benzyloxy-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane

Product 1

HCID 131730809Acetic acid 3-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl esterYield 85%

Procedure

A flask was charged with (6-Benzyloxy-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane, Acetic acid, acetic acid anhydride, and H2SO4. The reaction was stirred, extracted, and the solvent was evaporated to provide the titled compound in 85% yield.

Workup

  1. extractionextracted
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6202bd376f074e4db2347946b0153ca5
Source dataset
uspto-grants-2013_08
Patent number
US08513214B2

Reaction notes

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