Hydrochloric Acid → HCID 54499594, compound

HRID 265987Notes

Reaction equation

HRID 265987 reaction equation
[CH2:1]([Si:6]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10][CH:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:40][C:41]([F:51])([F:50])[O:42][C:43]1[CH:48]=[CH:47][C:46](O)=[CH:45][CH:44]=1.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[CH2:1]([Si:6]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10][CH:9]([C:12]([O:14][C:46]2[CH:45]=[CH:44][C:43]([O:42][C:41]([F:40])([F:50])[F:51])=[CH:48][CH:47]=2)=[O:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 70015p-(Trifluoromethoxy)phenolHCID 19032148HCID 19032148, compound

Product 1

HCID 54499594HCID 54499594, compoundYield 78.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 50 g of 4-n-pentyl-4-phenyl-4-silacyclohexanecarboxylic acid, 50.0 g of triphenylphosphine and 420 ml of carbon tetrachloride was agitated under reflux for 1 hour. Then, a mixture of 32.0 g of 4-trifluoromethoxyphenol and 100 ml of pyridine was added to the mixture, followed by further addition of 1.00 g of 4-dimethylaminopyridine and agitation at room temperature for 9 hours. The resultant reaction mixture was poured into dilute hydrochloric acid, followed by extraction with ethyl acetate. The ethyl acetate solution was washed with brine, dried and concentrated, followed by purification of the resultant residue with silica gel chromatography to obtain 60.8 g (yield: 78%) of (4-trifluoromethoxyphenyl) 4-n-pentyl-4-phenyl-4-silacyclohexanecarboxylate. The results of IR and NMR analyses are shown below.

Workup

  1. temperatureunder reflux for 1 hour
  2. additionwas added to the mixture
  3. customThe resultant reaction mixture
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe ethyl acetate solution was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customfollowed by purification of the resultant residue with silica gel chromatography

Sources & evidence

ORD record
ord-df2e6e15e311457b995f1e98e826e9d4
Source dataset
uspto-grants-1997_07
Patent number
US05650092

Reaction notes

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