Benzyl Bromide → HCID 21221308, compound

HRID 1735357Notes

Reaction equation

HRID 1735357 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH:3]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)(O)[O-].[K+]>CN(C)C=O>[CH2:21]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516893Potassium BicarbonateHCID 21221400HCID 21221400, compound

Product 1

HCID 21221308HCID 21221308, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-hydroxy-3-(3-benzyloxycarbonylpropyl)benzene (2.0 g), benzylbromide (1.14 ml), potassium bicabonate (1.53 g) and dimethylformamide (20 ml) was stirred for 3 h at room temperature. The mixture was quenched by addition of water and extracted with a mixture of n-hexane:ethyl acetate (3:1). 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 silica gel column chromatography (n-hexane:ethyl acetate=10:1) to give the title compound (2.55 g) having the following physical data.

Workup

  1. customThe mixture was quenched by addition of water
  2. extractionextracted with a mixture of n-hexane:ethyl acetate (3:1)
  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 silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-fa88d871e58b45d3a45eb90c16257df7
Source dataset
uspto-grants-1996_07
Patent number
US05536736

Reaction notes

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