2-(4-(4-Propylcyclohexyl)cyclohexyl)ethanol → Trifluoroacetic acid 2-(4-(4-propylcyclohexyl)cyclohexyl)-ethyl ester

HRID 2119275Notes

Reaction equation

HRID 2119275 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](C1C2N=NNC=2C=CC=1)=[O:4].[CH2:16]([CH:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][OH:33])[CH2:27][CH2:26]2)[CH2:21][CH2:20]1)[CH2:17][CH3:18]>C1COCC1>[CH2:16]([CH:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][O:33][C:3](=[O:4])[C:2]([F:15])([F:14])[F:1])[CH2:27][CH2:26]2)[CH2:21][CH2:20]1)[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 186495412-(4-(4-Propylcyclohexyl)cyclohexyl)ethanolHCID 178519451HCID 178519451, compound

Product 1

HCID 53895760Trifluoroacetic acid 2-(4-(4-propylcyclohexyl)cyclohexyl)-ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetylbenzotriazole in an amount of 7.0 g (33 mmol) was dissolved in 70 ml of THF, 5.0 g (20 mmol) of 2-(4-(4-propylcyclohexyl)cyclohexyl)ethanol was added thereto, they were refluxed for 1 hour, and then the solvent was distilled off. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=5/1), the solvent was distilled off, and the residue was subjected twice to recrystallization by using heptane to give 2.9 g (8.3 mmol) of trifluoroacetic acid 2-(4-(4-propylcyclohexyl)cyclohexyl)-ethyl ester. Yield of this compound based on 2-(4-(4-propylcyclohexyl)cyclohexyl)ethanol was 42%.

Workup

  1. temperaturethey were refluxed for 1 hour
  2. distillationthe solvent was distilled off
  3. customAfter the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=5/1)
  4. distillationthe solvent was distilled off
  5. customthe residue was subjected twice to recrystallization

Sources & evidence

ORD record
ord-04644beac639472a999f648f893b842b
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

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