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

HRID 1832415Notes

Reaction equation

HRID 1832415 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

(1R)-3-Chloro-1-phenyl-1-propanol (1.000 g, 5.86 mmol), 1-(3-hydroxyphenyl)ethanone (0.797 g, 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), 3.643.59 (m, 1H), 2.52 (s, 3H), 2.51–2.46 (m, 1H), 2.29–2.22 (m, 1H).

Workup

  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

Sources & evidence

ORD record
ord-d99bfb1d0ef24033a1a174e4646aaadf
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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