Water → Ethyl 2-[(E)-2-(2-quinolinyl)ethenyl]-1,3-thiazole-4-carboxylate

HRID 907381Notes

Reaction equation

HRID 907381 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11]P(=O)(OCC)OCC.[H-].[Na+].[CH:22]([C:24]1[S:25][CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=1)=O.O>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:22]/[C:24]1[S:25][CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11011347Diethyl 2-quinolinylmethylphosphonateHCID 11355896Ethyl 2-formyl-1,3-thiazole-4-carboxylate

Product 1

HCID 42611537Ethyl 2-[(E)-2-(2-quinolinyl)ethenyl]-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl 2-quinolinylmethylphosphonate (0.580 g, 2.08 mmol; see Preparation 13(i) above) was dissolved in anhydrous THF (2 mL), NaH (0.273 g, 11 mmol) was then added in small portions and the resulting solution allowed to stir for 10 min. Ethyl 2-formyl-1,3-thiazole-4-carboxylate (0.387 g, 2.08 mmol; see step (v) above) in anhydrous THF (3 mL) was added dropwise and the solution allowed to stir for 16 h. Water (5 mL) was then added (dropwise initially), during which time the sub-title compound precipitated as a light brown/yellow solid.

Workup

  1. stirringto stir for 16 h

Sources & evidence

ORD record
ord-633bdbb05e2b4b42881bc7135d4072e8
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

Loading…