Triethylamine → Difluoro-acetic acid 4-(4-ethylcyclohexyl)-cyclohexyl ester

HRID 2119276Notes

Reaction equation

HRID 2119276 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)[CH3:2].[F:16][CH:17]([F:21])[C:18](O)=[O:19].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([O:15][C:18](=[O:19])[CH:17]([F:21])[F:16])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9788Difluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 22242489(Trans,trans)-4'-ethyl-[1,1'-bi(cyclohexan)]-4-ol

Product 1

HCID 20615181Difluoro-acetic acid 4-(4-ethylcyclohexyl)-cyclohexyl esterYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In 30 ml of dichloromethane were dissolved 2.2 g (11 mmol) of 4-(4-ethylcyclohexyl)cyclohexanol, 1.9 g (20 mmol) of difluoroacetic acid, and 0.8 g (8 mmol) of triethylamine, and this solution was cooled down to 0° C. To this solution was added dropwise 15 ml of solution of 2.4 g (12 mmol) of dicyclohexylcarbodiimide (DCC) in dichloromethane, and the mixture was stirred at the same temperature for 1 hour and then at room temperature for 17 hours. After the crystals in the suspension thus obtained were filtered off, the solvent was distilled off under a reduced pressure. After the residue was purified by column chromatography on silica gel (eluent: heptane/toluene=1/1), the solvent was distilled off, and the residue was subjected twice to recrystallization to give 1.4 g (4.9 mmol) of difluoro-acetic acid 4-(4-ethylcyclohexyl)-cyclohexyl ester. Yield of this compound based on 4-(4-ethylcyclohexyl)cyclohexanol was 45%.

Workup

  1. waitat room temperature for 17 hours
  2. customAfter the crystals in the suspension thus obtained
  3. filtrationwere filtered off
  4. distillationthe solvent was distilled off under a reduced pressure
  5. customAfter the residue was purified by column chromatography on silica gel (eluent: heptane/toluene=1/1)
  6. distillationthe solvent was distilled off
  7. customthe residue was subjected twice to recrystallization

Sources & evidence

ORD record
ord-16258e70485e4ed2903df8b691651cc1
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

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