Water → HCID 11716098, compound

HRID 1840683Notes

Reaction equation

HRID 1840683 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=1.C(N(CC)CC)C.[Si:20](OS(C(F)(F)F)(=O)=O)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].O>ClCCl.C(OC(=O)C)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate

Product 1

HCID 11716098HCID 11716098, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxymethyl-benzoic acid methylester (2 gm) and triethylamine (3.36 mL) in dichloromethane (15 mL) was treated with t-butyldimethylsilyltriflate (4.47 gm) at −78° C. After 30 min the contents were allowed to warm up to the room temperature and continued the stirring for another 30 min. Water (30 mL) and ethylacetate (60 mL) were added to the reaction mixture and the organic layer was washed with 0.3 M KHSO4, water and brine, dried over MgSO4 and filtered. The solvent was evaporated and the residue was subjected to flash chromatography on silica column by eluting with 10% EtOAc/hexane to obtain 4-(t-butyldimethylsilyloxymethyl) benzoic acid methyl ester (3.3 gm, 95% yield).

Workup

  1. customstirring for another 30 min
  2. washthe organic layer was washed with 0.3 M KHSO4, water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. washby eluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-0d8cdeef84544ed1a9e8804927c3b017
Source dataset
uspto-grants-2004_01
Patent number
US06680311B1

Reaction notes

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