Tetrahydrofuran → HCID 178460464, compound

HRID 726509Notes

Reaction equation

HRID 726509 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]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:11][CH2:10]1.C(N(CC)CC)C.[O:28]1C[CH2:31][CH2:30][CH2:29]1.C(Cl)(=O)C=C>O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:29](=[O:28])[CH:30]=[CH2:31])[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 178520605HCID 178520605, compound

Product 1

HCID 178460464HCID 178460464, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 4.77 g of 2,3-difluoro-1-[trans-4-(5-hydroxypentyl)cyclohexyl]benzene, 1.9 g of triethylamine, and 60 ml of dry tetrahydrofuran were placed in a 100 ml flask. Then, 1.7 g of acryloyl chloride was added dropwise to the reaction mixture under ice water cooling, and the mixture was stirred at the same temperature for 4 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 3 g of 2,3-difluoro-1-[trans-4-(5-propenoyloxypentyl)cyclohexyl]benzene (Y: 52.9%). The compound thus obtained had a purity of 99.8% by GC, 99.2% by HPLC, and 1 spot by TLC. Furthermore, the compound had an m.p. of 29.6° C. to 30.7° 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-90c3b55c56e940898e354a3913e4327a
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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