Propanal → HCID 22345633, compound

HRID 584295Notes

Reaction equation

HRID 584295 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[C:4]([CH2:16][CH3:17])[CH:3]=1.C([Li])CCC.[CH:23](=[O:26])[CH2:24][CH3:25].[Cl-].[NH4+]>C1COCC1>[Si:7]([O:6][C:5]1[CH:14]=[CH:15][C:2]([CH:23]([OH:26])[CH2:24][CH3:25])=[CH:3][C:4]=1[CH2:16][CH3:17])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 527PropanalHCID 25517Ammonium ChlorideHCID 22345600HCID 22345600, compoundHCID 178418339Butyllithium

Product 1

HCID 22345633HCID 22345633, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

11.9 g (38 mmol) of (4-bromo-2-ethylphenoxy)-tert-butyldimethylsilane are placed in 200 ml of THF in a round-bottomed flask and under a stream of nitrogen. The reaction medium is cooled to −78° C. and 16.6 ml (41 mmol) of n-butyllithium (2.5 M/THF) are added dropwise. 30 minutes later, 3.2 ml (45 mmol) of propionaldehyde are added dropwise. The medium is stirred for 3 hours at −78° C. It is then poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. 11.1 g (100%) of the expected product are obtained in the form of a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-8c911ffc373343d1889a42a881e1fbdf
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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