4-trimethylsilylaniline → 12,12-Difluorododec-11-enoic acid N-(4-trimethylsilylphenyl)amide

HRID 1077706Notes

Reaction equation

HRID 1077706 reaction equation
CO[C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[C:14]([F:16])[F:15].[CH3:18][Si:19]([CH3:28])([CH3:27])[C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[CH3:18][Si:19]([CH3:28])([CH3:27])[C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[C:14]([F:15])[F:16])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 100349574-trimethylsilylanilineHCID 11149322Methyl 12,12-difluoro-11-dodecenoate

Product 1

HCID 1791256312,12-Difluorododec-11-enoic acid N-(4-trimethylsilylphenyl)amide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.5 g of 12,12-difluorododec-11-enoic acid methyl ester are added at room temperature to 1.53 g of 4-trimethylsilylaniline in 25 ml of toluene. The mixture is stirred for 2 hours at 80° and then concentrated by evaporation in vacuo. The residue is taken up in toluene, the toluene phase is washed with water, dried over sodium sulfate and concentrated to dryness by evaporation. The residue is taken up in hexane:ethyl acetate (9:1) and filtered over silica gel. Evaporation of the filtrate yields the title compound (nD24 =1.5038; compound no. 1-2).

Workup

  1. concentrationconcentrated by evaporation in vacuo
  2. washthe toluene phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness by evaporation
  5. filtrationfiltered over silica gel
  6. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-4aae1c82fbe04728bea68575e8343b34
Source dataset
uspto-grants-1996_08
Patent number
US05545630

Reaction notes

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