Tetrahydrofuran → HCID 18971050, compound

HRID 2395202Notes

Reaction equation

HRID 2395202 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][C:26]([F:38])([F:37])[C:27]([F:36])([F:35])[C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.C(N(CC)CC)C.[O:46]1C[CH2:49][CH2:48][CH2:47]1.C(Cl)(=O)C=C>O>[C:47]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][C:26]([F:37])([F:38])[C:27]([F:35])([F:36])[C:28]([F:33])([F:34])[C:29]([F:30])([F:31])[F:32])=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)(=[O:46])[CH:48]=[CH2:49]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 18971052HCID 18971052, compound

Product 1

HCID 18971050HCID 18971050, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask whose content had been replaced with Ar, 1.5 g of 4-(8-hydroxyoctyloxy)-4'-[2-(perfluorobutyl)ethyloxy]biphenyl, 0.3 g of triethylamine, and 16 ml of tetrahydrofuran were placed. While this solution was being cooled with ice water, 0.3 g of acryloyl chloride was added dropwise. The reaction solution was allowed to warm up to room temperature, and was stirred for 3 hours. Thereafter, the reaction solution was poured into water and an organic layer was extracted with benzene. After the benzene layer was washed with water and dried over sodium sulfate anhydrous, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: benzene), and recrystallized from acetone to give 0.7 g of 4-[8-(acryloyloxy)octyloxy]-4'-[2-(perfluorobutyl)ethyloxy]biphenyl (Y: 44.4%). The purity of the compound thus obtained was 98.4% by GC; 99.4% by HPLC; and 1 spot by TLC. The phase transition temperature of the resultant compound was as shown in Table 2 below.

Workup

  1. additionwas added dropwise
  2. extractionan organic layer was extracted with benzene
  3. washAfter the benzene layer was washed with water
  4. dry with materialdried over sodium sulfate anhydrous
  5. distillationthe solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: benzene)
  7. customrecrystallized from acetone

Sources & evidence

ORD record
ord-eb8b69166ff04960bed86e4711a1df8d
Source dataset
uspto-grants-1998_09
Patent number
US05814378

Reaction notes

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