Tetrahydrofuran → HCID 178460519, compound

HRID 726501Notes

Reaction equation

HRID 726501 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]([C@H:15]2[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]2)[CH2:11][CH2:10]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[CH2:19][CH2:20][C@H:15]([C@H:12]2[CH2:11][CH2:10][C@H:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])[CH2:14][CH2:13]2)[CH2:16][CH2:17]1)(=[O:29])[CH:31]=[CH2:32]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 178521562HCID 178521562, compound

Product 1

HCID 178460519HCID 178460519, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 1.44 g of trans-4-[trans-4-(2,3-difluorophenyl)cyclohexyl]cyclohexanol, 0.61 g of triethylamine, and 20 ml of dry tetrahydrofuran were placed in a 100 ml flask. Then, 0.53 g of acryloyl chloride was added dropwise to the mixture under ice water cooling. The resultant 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=1/2) and recrystallized from hexane to obtain 0.91 g of trans-4-[trans-4-(2,3-difluorophenyl)cyclohexyl]cyclohexyl acrylate (Y: 53.3%). The compound thus obtained had a purity of 98.8% by GC and 99.4% by HPLC. Furthermore, the phase transition temperature of this compound was as follows.

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=1/2)
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-e63c26bd787f48e6bd349777b793f80d
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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