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

HRID 2189966노트

반응식

HRID 2189966 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.[K+].[K+].[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 11430Potassium CarbonateHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-one

생성물 1

HCID 140682207-(Benzyloxy)-3,4-dihydronaphthalen-1(2H)-one수율 90.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 7-hydroxy-1-tetralone (1.0 g, 0.0061 mol) and K2CO3 (5.5 g) in DMF (20 mL) under an argon atmosphere was added benzyl bromide (0.725 mL, 0.0061 mol) at room temperature. The reaction mixture was then stirred at room temperature for 18 h before being poured onto ice. The aqueous solution was extracted with ethyl acetate, washed with water, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel using ethyl acetate-hexane (15%) as eluent to give compound 7-benzyloxy-1-tetralone (1.395 g, 90%): thick oil, 1H NMR (500 MHz, CDCl3): δ 2.09-2.14 (m, 2H), 2.63 (d, J=6.5 Hz, 2H), 2.90 (d, J=6.0 Hz, 2H), 5.75 (s, 2H), 7.11-7.13 (dd, J=3.0 and 8.5 Hz, 1H), 7.17 (d, J=8.5 Hz, 1H), 7.31-7.45 (m, 5H), 7.62 (d, J=3.0 Hz, 1H). HFABMS m/z 253.1231 (calc for C17H16O2, MH+, 253.1229).

후처리

  1. additionbefore being poured onto ice
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-8708c41bc4e54e93b27d0122572c17e1
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324262B2

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