Benzyl Bromide → HCID 21221308, compound

HRID 1585051Notes

Reaction equation

HRID 1585051 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-2d891c1347404f94a7515191a4bfaab1
Source dataset
uspto-grants-1999_08
Patent number
US05935985

Reaction notes

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