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

HRID 2087405ノート

反応式

HRID 2087405 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-6f6ec586555a4c639422f1ab9648a2d6
出典データセット
uspto-grants-2004_04
特許番号
US06727264B1

反応ノート

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