(S)-(-)-3-Chloro-1-phenyl-1-propanol → HCID 58630690, compound

HRID 1822981Notes

Reaction equation

HRID 1822981 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[C:18]2[S:19][CH:20]=[CH:21][C:17]=2[CH:16]=[CH:15][CH:14]=1>C1COCC1>[Cl:1][CH2:2][CH2:3][C@@H:4]([O:5][C:13]1[C:18]2[S:19][CH:20]=[CH:21][C:17]=2[CH:16]=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanolHCID 110840501-Benzothiophen-7-ol

Product 1

HCID 58630690HCID 58630690, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,4-(Dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-triphenyl phosphonium (1.15 g, 2.80 mmol) was added in one portion to a stirred solution of (S)-(−)-3-chloro-1-phenyl-1-propanol (317 mg, 1.86 mmol) and 7-hydroxybenzo[b]thiophene (280 mg, 1.86 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 (240 mg, 43%); Rf=0.78 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-c6e84e3c5643475e894584e2b88584c2
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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