Acetaldehyde → HCID 137329925, compound

HRID 1715422Notes

Reaction equation

HRID 1715422 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:19])([CH3:18])[C:8]1[CH:9]=[C:10]([CH2:15][CH2:16][NH2:17])[CH:11]=[CH:12][C:13]=1[Cl:14])([CH3:4])([CH3:3])[CH3:2].[CH:20](=O)[CH3:21].[BH4-].[Na+]>CO>[C:1]([SiH2:5][O:6][C:7]([CH3:19])([CH3:18])[C:8]1[CH:9]=[C:10]([CH2:15][CH2:16][NH:17][CH2:20][CH3:21])[CH:11]=[CH:12][C:13]=1[Cl:14])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 4311764Sodium borohydrideHCID 137329923HCID 137329923, compound

Product 1

HCID 137329925HCID 137329925, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethylamine (1.05 g, 3.50 mmol) and acetaldehyde (1.19 mL, 21.0 mmol) in MeOH (35 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt and NaBH4 (198 mg, 5.25 mmol) was added in portions. The mixture was stirred at rt for 1 h, and the solvents were removed under reduced pressure. The resulting oil was diluted with EtOAc, and the mixture was washed with aq. sat. NaHCO3 and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (CH2Cl2/MeOH 19:1→9:1) yielded the title compound (320 mg, 28%). LC-MS: tR=0.90 min; ES+: 369.22.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customthe solvents were removed under reduced pressure
  4. additionThe resulting oil was diluted with EtOAc
  5. washthe mixture was washed with aq. sat. NaHCO3 and brine
  6. dry with materiallayer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customPurification of the crude by FC (CH2Cl2/MeOH 19:1→9:1)

Sources & evidence

ORD record
ord-ad9ebb7ce3bd4cc394f1a203c61ca1b8
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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