Benzyl Bromide → 7-(Benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

HRID 1359015ノート

反応式

HRID 1359015 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-one

生成物 1

HCID 140682207-(Benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

7-Benzyloxy-3,4-dihydro-1(2H)naphthalenone was prepared by treating 7-hydroxy-1-tetralone (5.91 g, 36.4 mmol) and caesium carbonate (13 g, 40.0 mmol) in dry DMF (100 ml) and under N2 with benzylbromide (6.22 g, 4.33 ml, 36.4 mmol). The reaction was stirred for 3 h and the mixture then filtered and the filtrate concentrated in vacuo. The oily residue was partitioned between ethyl acetate (200 ml) and brine (200 ml), the organic layer separated, dried (MgSO4) and concentrated in vacuo. Trituration of the resultant solid with diethylether-hexane (1:1, 200 ml) gave the desired compound as a white solid (6.57 g) m.p. 86-87°0. MS (EI, 60V) 252 (M+, 100%).

後処理

  1. filtrationthe mixture then filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe oily residue was partitioned between ethyl acetate (200 ml) and brine (200 ml)
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-785644a7b80648f2a9b91f396aa336d1
出典データセット
uspto-grants-2003_07
特許番号
US06599908B1

反応ノート

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