Ethanol → HCID 137329840, compound

HRID 2242138Notes

Reaction equation

HRID 2242138 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:25])([CH3:24])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:17]=[O:18])([CH3:4])([CH3:3])[CH3:2].C(O)C.[BH4-].[Na+]>C(OCC)(=O)C>[C:1]([SiH2:5][O:6][C:7]([CH3:25])([CH3:24])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:15]=[C:16]([CH2:17][OH:18])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 137329841HCID 137329841, compound

Product 1

HCID 137329840HCID 137329840, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-4-yl]-4-methoxy-benzaldehyde (160 mg) was dissolved into ethanol (3 mL) and treated with sodium borohydride (85 mg). The reaction mixture was stirred for 1 hour, diluted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography to yield {3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-4-yl]-4-methoxy-phenyl}-methanol as a colorless oil.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-fe106eb5035e477ab3d87488a1a8a9d8
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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