Ethyl Acetate → HCID 178466165, compound

HRID 552591Notes

Reaction equation

HRID 552591 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28](=[O:30])[CH3:29])=[CH:21][C:15]=3[N:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CCOC(C)=O>C(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH:28]([OH:30])[CH3:29])=[CH:21][C:15]=3[N:14]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 178466164HCID 178466164, compound

Product 1

HCID 178466165HCID 178466165, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (E)-1-(2-{2-[2-(4-tert-butyl-phenyl)-vinyl]-1H-benzimidazol-5-yl}-phenyl)-ethanone Cpd 1 (0.005 g, 0.01 mmol) in ethanol (0.5 mL) was treated with NaBH4 (0.003 g, 0.08 mmol). After 3 h, the reaction mixture was applied to a preative TLC plate (2000 microns, silica gel, 20×20) and developed using EtOAc:hexanes, 1:1. The desired band was extracted and concentrated to give the title compound (0.002 g). 1H-NMR (400 MHz, CD3OD) δ (ppm) 7.69 (m, 1H) 7.62 (m, 3H) 7.50 (m, 3H) 7.41 (ddd, 2H, J=2.5 Hz, J=10.1 Hz, J=14.1 Hz) 7.32 (dt, 1H, J=1.4 Hz, J=7.5 Hz) 7.23 (m, 2H) 7.17 (d, 1H, J=16.5 Hz) 4.99 (q, 1H, J=6.3 Hz) 1.38 (s, 9H) 1.35 (d, 1.5H, J=6.1 Hz) 1.33 (d, 1.5H, J=6.1 Hz). MS (ESI, pos. ion) m/z: 397.2 (M+1).

Workup

  1. extractionThe desired band was extracted
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b28cec506e384e5c87ff375ed9a69ed0
Source dataset
uspto-grants-2011_05
Patent number
US07951829B2

Reaction notes

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