Tetrahydrofuran → HCID 178459098, compound

HRID 726497Notes

Reaction equation

HRID 726497 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[CH2:7][CH2:6]1.C(N(CC)CC)C.O1C[CH2:29][CH2:28][CH2:27]1.C(Cl)(=O)C=C>O>[CH:27]([O:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[CH2:9][CH2:10]1)=[CH:28][CH3:29]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 178520636HCID 178520636, compound

Product 1

HCID 178459098HCID 178459098, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 9.3 g of 1-[trans-4-(3-hydroxypropyl)cyclohexyl]-2,3-difluorobenzene, 4.1 g of triethylamine, and 100 ml of dry tetrahydrofuran were placed in a 200 ml flask. Then, 3.6 g of acryloyl chloride was added dropwise to the reaction mixture under ice water cooling. The 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 6 g of 1-[trans-4-(3-propenyloxypropyl)cyclohexyl]-2,3-difluorobenzene (Y: 53%). The compound thus obtained had a purity of 99.8% by GC, 100% by HPLC, and of 1 spot by TLC. Furthermore, the compound had an m.p. of 35.5° C. to 36.9° 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=2/3)
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-53af8ee094fd411a98730df9de8767ec
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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