Acetone → Methyl 3-methoxy-4,5-dimethyl-2-thiophenecarboxylate

HRID 621791ノート

反応式

HRID 621791 の反応式
O[C:2]1[C:6]([O:7][CH3:8])=[C:5](OC)[S:4][C:3]=1[C:11](OC)=O.[C:15](=[O:18])([O-])[O-].[K+].[K+].S([O:26][CH3:27])(OC)(=O)=O.[CH3:28]C(C)=O>>[CH3:8][O:7][C:6]1[C:2]([CH3:28])=[C:3]([CH3:11])[S:4][C:5]=1[C:15]([O:26][CH3:27])=[O:18]

参加物

5

反応物 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 54697142HCID 54697142、化合物

生成物 1

HCID 14154178Methyl 3-methoxy-4,5-dimethyl-2-thiophenecarboxylate

実験手順

Methyl 3-hydroxy-4,5-dimethoxy-2-thiophenecarboxylate (5.0 g, 27 mmoles) is dissolved in acetone (50 mL) under nitrogen. Potassium carbonate (4.5 g, 32 mmoles) is added followed by dimethyl sulfate (4.2 g, 32 mmoles) and the mixture is stirred and heated under reflux. After 18 hours the mixture is stripped of solvent under reduced pressure, and the residue is partitioned between water (100 mL) and dichloromethane (100 mL). After separation the aqueous layer is extracted with dichloromethane (75 mL). The combined organic extracts are washed twice with brine, dried over MgSO4, and stripped of solvent under reduced pressure. Recrystallization of the residue from pentane gave the product (3.4 g); mp 37°-39° C.

後処理

  1. temperatureheated
  2. temperatureunder reflux
  3. customthe residue is partitioned between water (100 mL) and dichloromethane (100 mL)
  4. customAfter separation the aqueous layer
  5. extractionis extracted with dichloromethane (75 mL)
  6. washThe combined organic extracts are washed twice with brine
  7. dry with materialdried over MgSO4
  8. customRecrystallization of the residue from pentane

出典と根拠

ORDレコード
ord-1b80725902b843b0941a23cba60288bd
出典データセット
uspto-grants-1989_04
特許番号
US04824958

反応ノート

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