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

HRID 1106569노트

반응식

HRID 1106569 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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°. MS (EI, 60 V) 252 (M+, 100%).

후처리

  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

출처 및 근거

ORD 기록
ord-6249b35e7b2844c191927fefcbe0f5c2
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057329

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