(S)-1-iodo-3-phenyl-3-propanol → 4-{[(1R)-3-Iodo-1-phenylpropyl]oxy}-1-benzothiophene-2-carbonitrile
Reaction equation
[I:1][CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].F[C:13]1[C:18]2[CH:19]=[C:20]([C:22]#[N:23])[S:21][C:17]=2[C:16](O)=[CH:15][CH:14]=1>C1COCC1>[I:1][CH2:2][CH2:3][C@@H:4]([O:5][C:13]1[C:18]2[CH:19]=[C:20]([C:22]#[N:23])[S:21][C:17]=2[CH:16]=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
Procedure
4,4-(Dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-triphenyl phosphonium (498 mg, 1.12 mmol) was added in one portion to a stirred solution of (S)-3-iodo-1-phenyl-1-propanol (Molander, Gary A.; Shakya, Sagar R.; J. Org. Chem.; 1994, 59; 12; 1994; 3445–3452) (237 mg, 0.84 mmol) and 4-fluoro-7-hydroxy-benzothiophene-2-carbonitrile (144 mg, 0.70 mmol) in dry THF (12 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 purified by flash chromatography with a gradient of 0–4% diethyl ether in hexane to give the title compound as a colourless oil (284 mg, 72%); δH (300 MHz, CDCl3) 7.83 (1H, s, 3-ArH), 7.36–7.12 (5H, m, ArH), 6.85–6.75 (1H, m, ArH), 6.65–6.57 (1H, m, ArH), 5.40–5.30 (1H, m, CHO), 3.47–3.28 (1H, m, CH2CHHI), 3.23–3.12 (1H, m, CH2CHHI), 2.60–2.42 (1H, m, CHHCH2I) and 2.34–2.19 (1H, m, CHHCH2I).
Workup
- customwas removed in vacuo
- customThe residue was purified by flash chromatography with a gradient of 0–4% diethyl ether in hexane
Sources & evidence
- ORD record
- ord-817e00173ae0454fb99ace69ffa0c59a
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07037932B2
Reaction notes
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