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

HRID 128805

反応式

HRID 128805 の反応式
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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7b48b71b05bd4cabba218c4052967b5b
出典データセット
uspto-grants-1995_11
特許番号
US05464865

関連ノート

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