Tetrahydrofuran → HCID 178460463, compound

HRID 726494Notes

Reaction equation

HRID 726494 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])[CH2:11][CH2:10]1.C(N(CC)CC)C.[O:30]1C[CH2:33][CH2:32][CH2:31]1.C(Cl)(=O)C=C>CCOCC>[C:31]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])[CH2:13][CH2:14]1)(=[O:30])[CH:32]=[CH2:33]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 178520600HCID 178520600, compound

Product 1

HCID 178460463HCID 178460463, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

First, 3.5 g of 1-[trans-4-(7-hydroxyheptyl)cyclohexyl]-2,3-difluorobenzene, 1.3 g of triethylamine, and 45 ml of dry tetrahydrofuran were placed in a 100 ml flask. Then, 1.1 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 for 1 hour. Ether was added to the reaction mixture. An ether layer was washed with water and dried over anhydrous sodium sulfate. A solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: benzene/hexane=3/7 to 4/6) and recrystallized from hexane to obtain 2.23 g of 1-[trans-4-(7-propenoyloxyheptyl)cyclohexyl]-2,3-difluorobenzene (Y: 54%). The compound thus obtained had a purity of 99.6% by GC, 99.5% by HPLC, and of 1 spot by TLC. Furthermore, the compound had an m.p. of 34.0° C. to 35.3° C.

Workup

  1. washAn ether layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationA solvent was distilled away
  4. customThe residue was purified by silica gel column chromatography (eluent: benzene/hexane=3/7 to 4/6)
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-b38bd24c1f634a558722a5e7c004f085
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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