3-(1-Tritylimidazol-4-YL) propionaldehyde → 1-(5-fluorobenzo[b]thiophen-2-yl)-3-(1-triphenylmethyl-1H-imidazol-4-yl)-propan-1-ol

HRID 2229261Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[Li]CCCC.[C:16]1([C:22]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:23]2[CH:27]=[C:26]([CH2:28][CH2:29][CH:30]=[O:31])[N:25]=[CH:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.[Cl-].[NH4+]>[F:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][C:7]([CH:30]([OH:31])[CH2:29][CH2:28][C:26]3[N:25]=[CH:24][N:23]([C:22]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:27]=3)=[CH:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 5-fluorobenzo[b]thiophene (1.22 g) in THF (22 ml) was added n-BuLi (1.6 M solution in hexane, 5.0 ml) at −78° C., and the mixture was stirred for 1 hour. To this mixture was added a solution of 3-(1-triphenylmethyl-1H-imidazole-4-yl)propanal (2.93 g) in THF (10 ml), and the mixture was allowed to warm to −40° C. over 1 hour. The mixture was diluted with 10% aqueous ammonium chloride, warmed to room temperature, and extracted with ethyl acetate. The extract was washed with brine, dried over MgSO4, and concentrated. The residue was chromatographed on silica gel using hexane-ethyl acetate (1:1) as an eluent to give the titled compound as colorless crystals (2.58 g).

Workup

temperaturewarmed to room temperature
extractionextracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-643722bb0a9f41fdb56f44091c46bd8b
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420375B1

Reaction notes

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