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

HRID 1799109Notes

Reaction equation

HRID 1799109 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f1c187a9cd5a4096b4646c7aaf1c658f
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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