Hydrochloric Acid → 2,3-Difluoro-4'-[12,12-bis(hydroxymethyl)dodecyl]oxybiphenyl

HRID 1289379ノート

反応式

HRID 1289379 の反応式
[BH4-].[Li+].O1CCCC1.Cl.[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([C:41](OCC)=[O:42])[C:36](OCC)=[O:37])=[CH:19][CH:18]=1>>[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([CH2:36][OH:37])[CH2:41][OH:42])=[CH:19][CH:18]=1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2 回HCID 4148881Lithium borohydrideHCID 189208382,3-Difluoro-4'-[12,12-bis(ethoxycarbonyl)dodecyl]oxybiphenyl

生成物 1

HCID 189208462,3-Difluoro-4'-[12,12-bis(hydroxymethyl)dodecyl]oxybiphenyl収率 71.6%

実験手順

First, 1.7 g of lithium borohydride and 20 ml of tetrahydrofuran were placed in a 100 ml flask. Then, 60 ml of tetrahydrofuran solution in which 4 g of 2,3-difluoro-4'-[12,12-bis(ethoxycarbonyl)dodecyl]oxybiphenyl was dissolved was added dropwise to the reaction mixture, and the resultant reaction mixture was stirred under reflux for 18 hours. The reaction mixture was poured into cold diluted hydrochloric acid, 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: ethyl acetate/toluene=8/2) and recrystallized from acetone to obtain 2.4 g of 2,3-difluoro-4'-[12,12-bis(hydroxymethyl)dodecyl]oxybiphenyl (Y: 71.6%). The compound thus obtained had a purity of 99.6% by HPLC.

後処理

  1. additionwas added dropwise to the reaction mixture
  2. customthe resultant reaction mixture
  3. temperatureunder reflux for 18 hours
  4. extractionan organic layer was extracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/toluene=8/2)
  9. customrecrystallized from acetone

出典と根拠

ORDレコード
ord-272f1f991dfc43899957c3fe45f07873
出典データセット
uspto-grants-1998_05
特許番号
US05750213

反応ノート

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