Water → HCID 23023484, compound

HRID 2222444Notes

Reaction equation

HRID 2222444 reaction equation
[OH:1][C:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)([CH2:8][OH:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].N1C(C)=CC=CC=1C.[C:27]([O:30][CH2:31]C)(=O)C.O>COC(OC)O>[OH:1][C:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)([CH2:8][O:9][CH2:27][O:30][CH3:31])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 8857Ethyl AcetateHCID 23023460HCID 23023460, compound

Product 1

HCID 23023484HCID 23023484, compound

Reagents, catalysts & solvents 1

HCID 17936250DimethoxymethanolSolvent

Procedure

A solution of 1.06 g of ethyl 2,3-dihydroxy-2-(4-methoxybenzyl)propanoate in 20 ml of dimethoxymethanol was cooled to 0° C. under an atmosphere of nitrogen gas. 0.94 g of 2,6-lutidine and 1.59 ml of 1,1,1-trimethylsilyl tri-fluoromethanesulfonate were sequentially added, and the mixture was stirred for 1 hour. 100 ml of ethyl acetate and 50 ml of water were added, and the organic layer was washed with 50 ml of brine, dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography, to give 1.00 g of the title compound as a colorless oil.

Workup

  1. washthe organic layer was washed with 50 ml of brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2180bfb936714e26a41030dbdcbabf1b
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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