Tetrahydrofuran → HCID 178460515, compound

HRID 726510Notes

Reaction equation

HRID 726510 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]1.C(N(CC)CC)C.[O:23]1C[CH2:26][CH2:25][CH2:24]1.C(Cl)(=O)C=C>O>[C:24]([O:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH2:10][CH2:11]1)(=[O:23])[CH:25]=[CH2:26]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 178521549HCID 178521549, compound

Product 1

HCID 178460515HCID 178460515, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 4.24 g of trans-4-(2,3-difluorophenyl)cyclohexanol, 2 g of triethylamine, and 60 ml of tetrahydrofuran were placed in a 100 ml flask. Then, 2.3 g of acryloyl chloride was added dropwise to the mixture under ice water cooling. The mixture was stirred at the same temperature for 3 hours. Water was added to the reaction mixture, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: benzene/hexane=1/1) and recrystallized from hexane to obtain 2.8 g of trans-4-(2,3-difluorophenyl)cyclohexyl acrylate (Y: 52.6%). The compound thus obtained had a purity of 99.9% by GC and 99.5% by HPLC. Furthermore, the compound had an m.p. of 72.9° C. to 73.6° C.

Workup

  1. extractionan organic layer was extracted with ether
  2. washThe ether layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThereafter, the solvent was distilled away
  5. customThe residue was purified by silica gel column chromatography (eluent: benzene/hexane=1/1)
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-5987429c551945a099f57d037f81d7dd
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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