4-Fluorobenzoyl chloride → HCID 178525712, compound

HRID 1463755Notes

Reaction equation

HRID 1463755 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[O:11]1[CH2:15][CH2:14][O:13][CH:12]1[CH2:16][CH2:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([C@H:24]2[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]2)[CH2:20][CH2:19]1>N1C=CC=CC=1>[O:11]1[CH2:15][CH2:14][O:13][CH:12]1[CH2:16][CH2:17][C@H:18]1[CH2:19][CH2:20][C@H:21]([C@H:24]2[CH2:29][CH2:28][C@H:27]([O:30][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:26][CH2:25]2)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 178521563HCID 178521563, compound

Product 1

HCID 178525712HCID 178525712, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.7 g of 4-fluorobenzoyl chloride in 5 ml of pyridine is treated with 2.8 g of trans-4-[trans-4-(2-(1,3-dioxolan-2-yl)ethyl)cyclohexyl]-cyclohexanol (prepared according to Example 3) and stirred at room temperature for 12 hours. Thereafter, the reaction mixture is poured on to ice-water and extracted three times with diethyl ether. The organic phases are washed in succession with saturated sodium hydrogen carbonate solution, with 10 percent hydrochloric acid, with saturated sodium hydrogen carbonate solution and with water, then dried over magnesium sulfate, filtered and concentrated. Chromatographic purification of the resulting crude product-on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gives 4-fluorobenzoic acid trans-4-[trans-4-[2-(1,3-dioxolan-2-yl)ethyl]cyclohexyl]-cyclohexyl ester.

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe organic phases are washed in succession with saturated sodium hydrogen carbonate solution, with 10 percent hydrochloric acid, with saturated sodium hydrogen carbonate solution and with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification of the resulting crude product-on silica gel with ethyl acetate/petroleum ether (vol. 3:97)

Sources & evidence

ORD record
ord-7c55e9b47fe24c88b05cdfa9a7d0a3be
Source dataset
uspto-grants-1994_04
Patent number
US05302317

Reaction notes

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