p-Toluenesulfonic acid monohydrate → Allyl (3'-fluoro-4'-{[2-formyl-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetate

HRID 2076603ノート

反応式

HRID 2076603 の反応式
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O:14][CH:15](OC)[C:16]1[C:43]([O:44]COC)=[C:42]([C:48]([F:51])([F:50])[F:49])[CH:41]=[CH:40][C:17]=1[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][CH2:36][CH:37]=[CH2:38])=[O:34])=[CH:28][CH:27]=2)=[CH:22][C:21]=1[F:39]>CC(C)=O>[F:39][C:21]1[CH:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][CH2:36][CH:37]=[CH2:38])=[O:34])=[CH:28][CH:27]=2)[CH:24]=[CH:25][C:20]=1[O:19][CH2:18][C:17]1[CH:40]=[CH:41][C:42]([C:48]([F:51])([F:50])[F:49])=[C:43]([OH:44])[C:16]=1[CH:15]=[O:14]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86617401Allyl (4'-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-3'-fluoro-1,1'-biphenyl-4-yl)acetate

生成物 1

HCID 86617402Allyl (3'-fluoro-4'-{[2-formyl-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetate収率 91.9%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
50 °C

実験手順

p-Toluenesulfonic acid monohydrate (223 mg, 1.18 mmol) was added to a solution of allyl (4′-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-3′-fluoro-1,1′-biphenyl-4-yl)acetate (618 mg, 1.06 mmol) obtained in Example (12-3) in acetone (10 ml), and the mixture was stirred at 50° C. for 1 hour. The residue obtained by concentrating the reaction mixture was diluted with ethyl acetate. The obtained solution was successively washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1) to give allyl (3′-fluoro-4′-{[2-formyl-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetate (476 mg, yield: 91%).

後処理

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture
  3. additionwas diluted with ethyl acetate
  4. washThe obtained solution was successively washed with a saturated aqueous sodium hydrogencarbonate solution, water
  5. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  6. customThe residue obtained
  7. customby removing the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-5bb9a4c216eb432c8fa4cf81b0e12ac4
出典データセット
uspto-grants-2011_04
特許番号
US07923573B2

反応ノート

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