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

HRID 1799109ノート

反応式

HRID 1799109 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f1c187a9cd5a4096b4646c7aaf1c658f
出典データセット
uspto-grants-2013_01
特許番号
US08343997B2

反応ノート

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