Trityl chloride → HCID 15428710, compound

HRID 1941286Notes

Reaction equation

HRID 1941286 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=1)[O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[C:19]1([C:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]2[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=2)[O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 21221403HCID 21221403, compound

Product 1

HCID 15428710HCID 15428710, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-(4-hydroxybutyl)phenoxyacetate (174 mg) in dimethylformamide (8.0 ml) was added successively trityl chloride (223 mg) and N,N-dimethylaminopyridine (88 mg). After stirred overnight at room temperature, the mixture was quenched by addition of water and extracted with ether. The extract was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by flash silica gel chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (228 mg) having the following physical data.

Workup

  1. customthe mixture was quenched by addition of water
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by flash silica gel chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9536edabd34c465fb9e7eb97ab963774
Source dataset
uspto-grants-1997_12
Patent number
US05703099

Reaction notes

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