Tetrahydrofuran → HCID 178460513, compound

HRID 726504Notes

Reaction equation

HRID 726504 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH2:14][CH2:13][CH:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]2)[CH2:11][CH:10]=1.C(N(CC)CC)C.[O:29]1C[CH2:32][CH2:31][CH2:30]1.C(Cl)(=O)C=C>O>[C:30]([O:21][C@H:18]1[CH2:17][CH2:16][C@H:15]([CH:12]2[CH2:13][CH2:14][C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])=[CH:10][CH2:11]2)[CH2:20][CH2:19]1)(=[O:29])[CH:31]=[CH2:32]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 178521546HCID 178521546, compound

Product 1

HCID 178460513HCID 178460513, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 4.6 g of trans-4-[4-(2,3-difluorophenyl)-3-cyclohexenyl]cyclohexanol, 1.76 g of triethylamine, and 60 ml of dry tetrahydrofuran were placed in a 100 ml flask. Then, 1.57 g of acryloyl chloride was added dropwise to the reaction mixture under ice water cooling. The resultant reaction mixture was allowed to warm to room temperature and stirred overnight. 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=2/3) and recrystallized from hexane to obtain 2.74 g of trans-4-[4-(2,3-difluorophenyl)-3-cyclohexenyl]cyclohexyl acrylate (Y: 50.4%). The compound thus obtained had a purity of 99.8% by HPLC and 1 spot by TLC. Furthermore, the phase transition temperature of the compound was as follows.

Workup

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

Sources & evidence

ORD record
ord-dfe491d6ae0c4816b571b01cc7973f0f
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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