2-Naphthyl glycidyl ether → 1-(2-Hydroxy-3-(2-naphthyloxy)propyl)-4-(2-methoxyethenyl)benzene

HRID 128805

반응식

HRID 128805 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][O:10][CH3:11])=[CH:4][CH:3]=1.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[O:22][CH2:23][CH:24]1[CH2:26][O:25]1>>[OH:25][CH:24]([CH2:23][O:22][C:13]1[CH:14]=[CH:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=1)[CH2:26][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][O:10][CH3:11])=[CH:4][CH:3]=1

참가 물질

3

반응물 2

HCID 929952-Naphthyl glycidyl etherHCID 534071961-Bromo-4-(2-methoxyvinyl)benzene

생성물 1

HCID 536460731-(2-Hydroxy-3-(2-naphthyloxy)propyl)-4-(2-methoxyethenyl)benzene수율 57.8%

실험 절차

By the method of example 48, 1-bromo-4-(2-methoxyethenyl)benzene (2.13 g) is lithiated and reacted with (2-naphthyloxymethyl)oxirane (2.0 g). The reaction mixture is allowed to warm to room temperature and stirred for 48 hr before quenching with saturated ammonium chloride. The product is extracted with ether, and the extract is dried and concentrated to leave 1-(2-hydroxy-3-(2-naphthyloxy)propyl)-4-(2-methoxyethenyl)benzene as a yellow oil (1.93 g). By the methods of example 1, this is converted into the title compound, which is obtained as a colorless solid, mp 175°-178° after recrystallization from hexane-ethyl acetate. This material is racemic at the propyl carbinol carbon, but substitution of a chiral form of the starting oxirane provides the title compound in chiral form.

후처리

  1. custombefore quenching with saturated ammonium chloride
  2. extractionThe product is extracted with ether
  3. customthe extract is dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7b48b71b05bd4cabba218c4052967b5b
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464865

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