Hydrochloric Acid → HCID 131719802, compound

HRID 234556Notes

Reaction equation

HRID 234556 reaction equation
[C:1]1([Si:7]2(CCC)[CH2:12][CH2:11][CH:10]([CH:13]3[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:30]=CC=C[CH:26]=1.[F:44][C:45]1[CH:50]=[CH:49][C:48](O)=[CH:47][CH:46]=1.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[C:1]1([SiH:7]2[CH2:8][CH2:9][C:10]([CH2:26][CH2:25][CH3:30])([CH:13]3[CH2:14][CH2:15][CH:16]([C:19]([O:21][C:48]4[CH:49]=[CH:50][C:45]([F:44])=[CH:46][CH:47]=4)=[O:20])[CH2:17][CH2:18]3)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 23354836HCID 23354836, compound

Product 1

HCID 131719802HCID 131719802, compoundYield 70.2%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 3.58 g of 4-(4-phenyl-4-n-propyl-4-silacyclohexyl)cyclohexanecarboxylic acid, 3.0 g of triphenylphosphine and 50 ml of carbon tetrachloride was agitated under reflux for 6 hours. Then, a mixture of 1.50 g of 4-fluorophenol and 10 ml of pyridine was added to the mixture, followed by further addition of 50 mg of 4-dimethylaminopyridine and agitation at room temperature for 18 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 3.20 g (yield: 70%) of 4-fluorophenyl 4-(4-phenyl-n-propyl-4-silacyclohexyl)cyclohexanecarboxylate. The results of

Workup

  1. temperatureunder reflux for 6 hours
  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-c757cfd613114a6dba637692df4b1a13
Source dataset
uspto-grants-1997_01
Patent number
US05595686

Reaction notes

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