Water → HCID 18920860, compound

HRID 1289388Notes

Reaction equation

HRID 1289388 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=2[F:32])=[CH:21][CH:20]=1)=[O:10].C(N(CC)CC)C.[O:47]1[CH2:51][CH2:50][CH2:49]C1.O.[C:53](Cl)(=[O:56])[CH:54]=[CH2:55]>>[C:53]([O:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][C:51](=[O:47])[CH:50]=[CH2:49])[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=2[F:32])=[CH:21][CH:20]=1)=[O:10])(=[O:56])[CH:54]=[CH2:55]

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 18920865HCID 18920865, compound

Product 1

HCID 18920860HCID 18920860, compoundYield 28%

Procedure

First, 2.6 g of 6-[2,3-difluorobiphenyl-4'-yl]oxyhexyl 2,2-bis(6-hydroxyhexyl)acetate, 1.2 g of triethylamine, and 100 ml of tetrahydrofuran were placed in a 200 ml flask. Then, a small amount of tetrahydrofuran in which 1.1 g of acryloyl chloride was dissolved was added dropwise to the mixture under ice water cooling. The resultant mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was poured into water, and an organic layer was extracted with ether. The ether layer was washed with diluted hydrochloric acid and water in this order, and then dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/toluene=1/9) to obtain 0.9 g of 6-[2,3difluorobiphenyl-4'-yl]oxyhexyl 2,2-bis(6-acryloyloxyhexyl)acetate (Y: 28%). The compound thus obtained was liquid at room temperature. The compound thus obtained had a purity of 99% by HPLC and of 1 spot by TLC.

Workup

  1. additionwas added dropwise to the mixture under ice water cooling
  2. extractionan organic layer was extracted with ether
  3. washThe ether layer was washed with diluted hydrochloric acid and water in this order
  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: ethyl acetate/toluene=1/9)

Sources & evidence

ORD record
ord-7a8b29a354664a5baded164eeee2d7bd
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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