Epibromohydrin → 2-{2-[4-(2-Benzyloxyphenyl)-1-buten-1-yl]phenoxymethyl}oxirane

HRID 743213Notes

Reaction equation

HRID 743213 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][C:27](C)([O-:29])[CH3:28].[K+].C(C1OC1)Br>CC(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH:27]1[CH2:28][O:29]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 23665647Potassium tert-butoxideHCID 54252394HCID 54252394, compound

Product 1

HCID 540152802-{2-[4-(2-Benzyloxyphenyl)-1-buten-1-yl]phenoxymethyl}oxiraneYield 85%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 1(a), 330 mg of 2-[4-(2-benzyloxyphenyl)-1-buten-1-yl)phenol (prepared as described in Preparation 14), 124 mg of potassium t-butoxide and 151 mg of epibromohydrin were reacted in 10 ml of dimethylacetamide. The crude product, extracted as described in Example 1(a), was purified as described in Example 1(a), to give 328 mg (yield 85%) of the title compound as a colorless oil.

Workup

  1. extractionThe crude product, extracted
  2. customwas purified

Sources & evidence

ORD record
ord-44c7f70a74cb4973b235a6386804ab3d
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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