Ammonium Chloride → 1-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-(1E)-undecen-3-one

HRID 977590Notes

Reaction equation

HRID 977590 reaction equation
COP([CH2:7][C:8](=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=O)OC.[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH:30]=O)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[Cl-].[NH4+]>O1CCCC1>[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[C:29](/[CH:30]=[CH:7]/[C:8](=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:32]=[CH:33][CH:34]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 13939083Dimethyl (2-oxodecyl)phosphonateHCID 156617653-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]Benzaldehyde

Product 1

HCID 156617891-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-(1E)-undecen-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

For Wittig-Horner olefination, 3.64 g of potassium-tertbutylate is added at -20° C. to a solution of 9.41 g of-2-oxo-decyl-phosphonic acid dimethyl ester in 280 ml of tetrahydrofuran and stirred for 20 minutes at this temperature. Then, a solution of 4.5 g of 3-tert-butyldimethylsilyloxymethylbenzaldehyde (see example 18A) in 150 ml of tetrahydrofuran is instilled in this solution and stirred for one hour at -20° C. It is poured on 500 ml of saturated ammonium chloride solution, extracted with ethyl acetate, the organic phase is washed neutral with brine, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue thus obtained is chromatographed on silica gel. With hexane/5-20% ethyl acetate, 6.5 g of 1-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-(1E)-undecen-3-one is obtained as colorless oil.

Workup

  1. stirringstirred for one hour at -20° C
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is washed neutral with brine
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue thus obtained
  7. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-16214ab528a1461bb87c5bd0ee4b420e
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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