Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate → Ethyl 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylate

HRID 453295노트

반응식

HRID 453295 반응식
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

참가 물질

3

반응물 1

HCID 67425118Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate

생성물 1

HCID 67425119Ethyl 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylate수율 88%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate (26.1 g, 86.6 mmol) was dissolved in EtOAc (350 mL) and hydrogenated under balloon pressure for four days until LCMS indicated complete reduction of unsaturation. On day three, the catalyst was removed by filtration, fresh catalyst added and the mixtures re-subjected to hydrogenation at balloon pressure. The catalyst was removed by filtration through a pad of celite. The filter pad was rinsed with EtOAc and the filtrate concentrated to dryness. The crude product was purified by MPLC eluting with pentane/EtOAc to give ethyl 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylate (23.2 g, 88% yield).

후처리

  1. waitOn day three
  2. customthe catalyst was removed by filtration, fresh catalyst
  3. additionadded
  4. customThe catalyst was removed by filtration through a pad of celite
  5. washThe filter pad was rinsed with EtOAc
  6. concentrationthe filtrate concentrated to dryness
  7. customThe crude product was purified by MPLC
  8. washeluting with pentane/EtOAc

출처 및 근거

ORD 기록
ord-43d328e5a4f747e6bfd22ab04792e82f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492401B2

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