Phenethyl bromide → 6-(2-Phenylethoxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63085노트

반응식

HRID 63085 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.Br[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:16]1([CH2:15][CH2:14][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

생성물 1

HCID 130673316-(2-Phenylethoxy)-1,2,3,4-tetrahydronaphthalen-1-one수율 61.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 6-hydroxy-3,4-dihydro-1(2H)-naphthalenone (2.0 g, 12.3 mmol) and (2-bromoethyl)benzene (4.8 g, 25.8 mmol) in ACN (20 mL) was added potassium carbonate (3.4 g, 24.6 mmol) at rt. The solution was heated at reflux overnight. The reaction was filtered, concentrated, and purified by silica gel chromatography (PE/EtOAc/DCM=10:1:2) to give 2.0 g (61%) of the title compound as a brown oil. 1H NMR (300 MHz, CDCl3): δ 2.08-2.16 (2H, m), 2.62 (2H, t, J=6.3 Hz), 2.92 (2H, t, J=6.3 Hz), 3.13 (2H, t, J=7.2 Hz), 2.92 (2H, t, J=7.2 Hz), 6.71 (1H, d, J=2.1 Hz), 6.83 (1H, dd, J=2.4, 8.7 Hz), 7.27-7.38 (5H, m), 8.01 (1H, dd, J=8.7 Hz).

후처리

  1. temperatureThe solution was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (PE/EtOAc/DCM=10:1:2)

출처 및 근거

ORD 기록
ord-af7c815808a2477ab142ff286c75a0cd
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447045B2

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