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

HRID 2229261
Notes
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Reaction equation

HRID 2229261 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 114514283-(1-Tritylimidazol-4-YL) propionaldehydeHCID 118159505-Fluoro-1-benzothiopheneHCID 178418339Butyllithium

Product 1

HCID 184669791-(5-fluorobenzo[b]thiophen-2-yl)-3-(1-triphenylmethyl-1H-imidazol-4-yl)-propan-1-olYield 62.2%

Reagents, catalysts & solvents 2

HCID 8028Tetrahydrofuran
Solvent
2×
HCID 25517Ammonium ChlorideSolvent

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

  1. temperaturewarmed to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes