Allyl bromide → HCID 86617396、化合物

HRID 2076589ノート

反応式

HRID 2076589 の反応式
O.[C:2]1(C)C=CC(S(O)(=O)=O)=C[CH:3]=1.C[O:14][CH:15](OC)[C:16]1[C:40]([O:41][CH2:42]OC)=[C:39]([C:45]([F:48])([F:47])[F:46])[CH:38]=[CH:37][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][CH3:36])=[O:34])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(Br)C=C>CC(C)=O.CN(C)C=O.O>[CH2:42]([O:41][C:40]1[C:16]([CH:15]=[O:14])=[C:17]([CH:37]=[CH:38][C:39]=1[C:45]([F:46])([F:47])[F:48])[CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:30][CH:31]=2)=[CH:24][CH:25]=1)[CH:2]=[CH2:3]

参加物

8

反応物 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86617395Methyl (4'-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetate

生成物 1

HCID 86617396HCID 86617396、化合物収率 84%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

After p-toluenesulfonic acid monohydrate (1.01 g, 5.31 mmol) was added to a solution of methyl (4′-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetate (2.38 g, 4.45 mmol) obtained in Example (6-7) in acetone (14 ml), the mixture was stirred at room temperature for 14 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a residue. Potassium carbonate (738 mg, 5.34 mmol) and allyl bromide (0.462 ml, 5.34 mmol) were successively added to a solution of the obtained residue in N,N-dimethylformamide (4 ml) and the mixture was stirred at 50° C. for 2 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, the organic layer was successively washed with 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=50/1-2/1) to give methyl (4′-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetate (1.81 g, yield: 84%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto give a residue
  6. stirringthe mixture was stirred at 50° C. for 2 hours
  7. extractionthe mixture was extracted with ethyl acetate
  8. washthe organic layer was successively washed with water
  9. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  10. customThe residue obtained
  11. customby removing the solvent under reduced pressure
  12. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=50/1-2/1)

出典と根拠

ORDレコード
ord-919d50fe785b46a69c2e9a3366eee52d
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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