Hydrochloric Acid → 2-(3-Methoxyphenyl)-cyclopentanol

HRID 377305

反応式

HRID 377305 の反応式
[O:1]1[CH:3]2[CH2:4][CH2:5][CH2:6][CH:2]12.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([Mg]Br)[CH:12]=[CH:13][CH:14]=1.C(OCC)(=O)C.Cl>O1CCCC1.[Cu]Cl>[OH:1][CH:3]1[CH2:4][CH2:5][CH2:6][CH:2]1[C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([O:8][CH3:7])[CH:14]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 178490745HCID 178490745、化合物

生成物 1

HCID 27596482-(3-Methoxyphenyl)-cyclopentanol

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of a mixture of 1,2-epoxycyclopentane (7.0 g) and copper(I) chloride (260 mg) in tetrahydrofuran (70 ml) was added 3-methoxyphenylmagnesium bromide (53.5 m mol) in tetrahydrofuran (60 ml) at -78° C. under N2. The mixture was stirred for 1 hour at 0° C. The reaction mixture was poured into a mixture of ethyl acetate and 1N-hydrochloric acid and then the organic layer was washed with saturated sodium bicarbonate aqueous solution and brine. The combined organic extracts were concentrated and the residue was purified by column chromatography on silica gel to give 1-hydroxy-2-(3-methoxyphenyl)-cyclopentane (13 g).

後処理

  1. washthe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  2. concentrationThe combined organic extracts were concentrated
  3. customthe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-3474d8f17eb34a109a738bd51f4697eb
出典データセット
uspto-grants-2000_02
特許番号
US06025375

関連ノート

読み込み中…