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Methanol → [4-isobutoxy-3-[(2-phenyl-1H-indol-1-yl)methyl]phenyl}methanol

HRID 2110852
Notes
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Reaction equation

HRID 2110852 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[CH2:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:2]([CH3:4])[CH3:3].CO.O1CCCC1.[BH4-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][C:7]=1[CH2:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:2]([CH3:4])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 231599294-isobutoxy-3-[(2-phenyl-1H-indol-1-yl)methyl]benzaldehyde

Product 1

HCID 23159990[4-isobutoxy-3-[(2-phenyl-1H-indol-1-yl)methyl]phenyl}methanolYield 99.8%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-isobutoxy-3-[(2-phenyl-1H-indol-1-yl)methyl]benzaldehyde (0.6 g, 1.56 mmol), methanol (3 mL) and tetrahydrofuran (6 mL) was added sodium borohydride (30 mg, 0.78 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 1.5 hr. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, and the mixture washed with 5% aqueous potassium hydrogensulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/1) to give the title compound (0.60 g, yield 99%) as a colorless oil. 1H NMR (CDCl3) δ: 1.00 (6H, d, J=6.6 Hz), 1.37 (1H, t, J=6.0 Hz), 2.09 (1H, m), 3.79 (2H, d, J=6.6 Hz), 4.40 (2H, d, J=6.0 Hz), 5.36 (2H, s), 6.62 (1H, d, J=1.8 Hz), 6.68 (1H, s), 6.88 (1H, d, J=8.1 Hz), 7.10-7.18 (3H, m), 7.23 (1H, d, J=2.1, 8.4 Hz), 7.29-7.48 (5H, m), 7.68 (1H, m).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1.5 hr
  2. customAfter completion of the reaction
  3. washthe mixture washed with 5% aqueous potassium hydrogensulfate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a6b1f2c029f443b2801a1b04931b2a15
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07517910B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes