3-Hydroxyacetophenone → 1-(3-{[(1S)-3-chloro-1-phenylpropyl]oxy}phenyl)ethanone

HRID 2087405노트

반응식

HRID 2087405 반응식
[Cl:1][CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].O[C:13]1[CH:14]=[C:15]([C:19](=[O:21])[CH3:20])[CH:16]=[CH:17][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[Cl:1][CH2:2][CH2:3][C@H:4]([O:5][C:13]1[CH:14]=[C:15]([C:19](=[O:21])[CH3:20])[CH:16]=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 4

HCID 84873-HydroxyacetophenoneHCID 11776TriphenylphosphineHCID 642409(1R)-3-chloro-1-phenylpropan-1-olHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 695236581-(3-{[(1S)-3-chloro-1-phenylpropyl]oxy}phenyl)ethanone수율 76%

실험 절차

(1R)-3-Chloro-1-phenyl-1-propanol (1.000 g, 5.86 mmol), 1-(3-hydroxyphenyl)ethanone (0.797 9, 5.86 mmol), triphenylphosphine (1.54 g, 5.86 mmol) and diethylazodicarboxylate (1.53 g, 8.79 mmol) were combined in a flask, which was immediately flushed with argon. THF (20 mL) was added and the mixture was stirred overnight under argon. THF was removed in vacuo, the crude product was dissolved in 50 mL of CH2Cl2/H2O (1:1) and the organic layer was separated and dried over MgSO4. After removing the solvent in vacuo, the residue was purified by flash chromatography using 10% ethyl acetate/hexane to yield the desired product (900 mg, 76.0%): 1H NMR (400 MHz, CDCl3) δ 7.49-7.46 (m, 2H), 7.40-7.26 (m, 6H), 7.07-7.04 (m, 1H), 5.46-5.43 (dd, 1H, J=4.4 Hz, 8.8 Hz), 3.84-3.78 (m, 1H), 3.64-3.59 (m, 1H), 2.52 (s, 3H), 2.51-2.46 (m, 1H), 2.29-2.22 (m, 1H).

후처리

  1. customwhich was immediately flushed with argon
  2. additionTHF (20 mL) was added
  3. customTHF was removed in vacuo
  4. dissolutionthe crude product was dissolved in 50 mL of CH2Cl2/H2O (1:1)
  5. customthe organic layer was separated
  6. dry with materialdried over MgSO4
  7. customAfter removing the solvent in vacuo
  8. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-6f6ec586555a4c639422f1ab9648a2d6
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06727264B1

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