(1R)-3-chloro-1-phenylpropan-1-ol → 7-[(1S)-3-Chloro-1-phenylpropyl]oxy-1-benzothiophene

HRID 1822979Notes

Reaction equation

HRID 1822979 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].[S:12]1[C:16]2[C:17](O)=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[CH:13]1>C1COCC1>[Cl:1][CH2:2][CH2:3][C@H:4]([O:5][C:17]1[C:16]2[S:12][CH:13]=[CH:14][C:15]=2[CH:20]=[CH:19][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 642409(1R)-3-chloro-1-phenylpropan-1-olHCID 110840501-Benzothiophen-7-ol

Product 1

HCID 586306737-[(1S)-3-Chloro-1-phenylpropyl]oxy-1-benzothiopheneYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,4-(Dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-triphenyl phosphonium (327 mg, 0.80 mmol) was added in one portion to a stirred solution of (R)-(+)-3-chloro-1-phenyl-1-propanol (90 mg, 0.53 mmol) and 1-benzothiophen-7-ol (80 mg, 0.53 mmol) in dry THF (5 mL) under an inert atmosphere on nitrogen. The resulting suspension was allowed to stir for a further 18 hrs before the solvent was removed in vacuo. The residue was triturated with hexane (ca. 15 mL) and the solid filtered, the filtrate was concentrated in vacuo and the resulting pale yellow oil was purified by flash chromatography eluting silica gel with hexane:ether [95:5] to yield the title compound as a colourless oil (60 mg, 37%); Rf=0.8 in hexane:ether [10:1]; δH (300 MHz, CDCl3) 7.66–7.00 (9H, m, Ar); 6.55 (1H, d, Ar), 5.80–5.72 (1H, m, CHO), 3.91–3.60 (2H, m, CH2), 2.62–2.50 (1H, m, CHH), 2.38–2.22 (1H, m, CHH).

Workup

  1. customwas removed in vacuo
  2. customThe residue was triturated with hexane (ca. 15 mL)
  3. filtrationthe solid filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe resulting pale yellow oil was purified by flash chromatography
  6. washeluting silica gel with hexane

Sources & evidence

ORD record
ord-9205fcf432d44ad2af6c08539855739e
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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