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

HRID 621793노트

반응식

HRID 621793 반응식
[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]

참가 물질

4

반응물 2

HCID 587860Methyl 3-hydroxy-5-methylthiophene-2-carboxylateHCID 178457939HCID 178457939, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-77e179ef37c741b8a1068b75926a9b3d
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04824958

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