Methyl 3-hydroxy-5-methylthiophene-2-carboxylate → Methyl 3-(1-methylethoxy)-5-methyl-2-thiophenecarboxylate

HRID 621793ノート

反応式

HRID 621793 の反応式
[OH:1][C:2]1[CH:6]=[C:5]([CH3:7])[S:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9].[CH:12](N=C(O)N(C(C)C)C(C)C)([CH3:14])[CH3:13]>C(#N)C>[CH3:13][CH:12]([O:1][C:2]1[CH:6]=[C:5]([CH3:7])[S:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9])[CH3:14]

参加物

4

反応物 2

HCID 587860Methyl 3-hydroxy-5-methylthiophene-2-carboxylateHCID 178457939HCID 178457939、化合物

生成物 1

HCID 14423925Methyl 3-(1-methylethoxy)-5-methyl-2-thiophenecarboxylate収率 75.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Methyl 3-hydroxy-5-methyl-2-thiophenecarboxylate (20.0 g, 116 mmoles) is dissolved in acetonitrile (450 mL) under argon. Triisopropylisourea (86.6 g, 465 mmoles) is added and the mixture stirred and heated under reflux. After 24 hours the mixture is cooled and the precipitate filtered off, rinsed with cold MeCN and discarded. The filtrate is stripped of solvent by rotary evaporator, then the excess triisopropylisourea is removed by distillation under reduced pressure. The remaining residue is dissolved in a small amount of ethyl acetate, cooled, filtered, and passed through a short column of silica gel. Evaporation of the effluent under reduced pressure leaves the product as an oil (18.8 g) sufficiently pure for further use.

後処理

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureAfter 24 hours the mixture is cooled
  4. filtrationthe precipitate filtered off
  5. washrinsed with cold MeCN
  6. customThe filtrate is stripped of solvent by rotary evaporator
  7. customthe excess triisopropylisourea is removed by distillation under reduced pressure
  8. dissolutionThe remaining residue is dissolved in a small amount of ethyl acetate
  9. temperaturecooled
  10. filtrationfiltered
  11. customEvaporation of the effluent under reduced pressure

出典と根拠

ORDレコード
ord-77e179ef37c741b8a1068b75926a9b3d
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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