Methyl 5-[(3-chlorophenyl)methyl]-4-{2-[(1,1-dimethylethyl)dimethylsilyl]oxyethoxy}thiophene-3-carboxylate → 5-[(3-Chlorophenyl)methyl]4-{2-[(1,1-dimethylethyl)dimethylsilyl]oxyethoxy}thiophene-3-carboxylic acid

HRID 1835170ノート

反応式

HRID 1835170 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]2[S:13][CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[C:10]=2[O:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:5]=[CH:6][CH:7]=1>[OH-].[Li+].CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]2[S:13][CH:12]=[C:11]([C:14]([OH:16])=[O:15])[C:10]=2[O:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 1

HCID 23503266Methyl 5-[(3-chlorophenyl)methyl]-4-{2-[(1,1-dimethylethyl)dimethylsilyl]oxyethoxy}thiophene-3-carboxylate

生成物 1

HCID 235032315-[(3-Chlorophenyl)methyl]4-{2-[(1,1-dimethylethyl)dimethylsilyl]oxyethoxy}thiophene-3-carboxylic acid収率 42.5%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 3939Lithium Hydroxide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 5-[(3-chlorophenyl)methyl]-4-{2-[(1,1-dimethylethyl)dimethylsilyl]oxyethoxy}thiophene-3-carboxylate (10.2 g) was dissolved in a mixture of 1M lithium hydroxide (50 ml), methanol (50 ml) and tetrahydrofuran (150 ml) and stirred for 18 hr. The reaction mixture was concentrated and the residue was partitioned between dichloromethane and 2M hydrochloric acid. The organic layer was collected, dried and filtered. t-Butyl-dimethylsilyl chloride (7 g) and imidazole (3.1 g) were added to the solution and the mixture was stirred for 72 hours. The reaction mixture was concentrated and the residue was dissolved in methanol. Potassium carbonate (5 g) was added to the solution and the suspension was vigorously stirred for 3 minutes, then filtered and concentrated. The residue was dissolved in ethyl acetate, washed with 2M hydrochloric acid, dried, filtered and concentrated. The residue was purified by chromatography, eluting with 10:1:1 isohexane:ethyl acetate:acetic acid, to give the sub-title compound (4.2 g).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between dichloromethane and 2M hydrochloric acid
  3. customThe organic layer was collected
  4. customdried
  5. filtrationfiltered
  6. additiont-Butyl-dimethylsilyl chloride (7 g) and imidazole (3.1 g) were added to the solution
  7. stirringthe mixture was stirred for 72 hours
  8. concentrationThe reaction mixture was concentrated
  9. dissolutionthe residue was dissolved in methanol
  10. additionPotassium carbonate (5 g) was added to the solution
  11. stirringthe suspension was vigorously stirred for 3 minutes
  12. filtrationfiltered
  13. concentrationconcentrated
  14. dissolutionThe residue was dissolved in ethyl acetate
  15. washwashed with 2M hydrochloric acid
  16. customdried
  17. filtrationfiltered
  18. concentrationconcentrated
  19. customThe residue was purified by chromatography
  20. washeluting with 10:1:1 isohexane

出典と根拠

ORDレコード
ord-0477a94ef6794d45b557dfe2fe34ff81
出典データセット
uspto-grants-2004_08
特許番号
US06770646B2

反応ノート

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