Triethyl phosphonoacetate → HCID 67526446, compound

HRID 992994Notes

Reaction equation

HRID 992994 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:29]2[S:30][CH:31]=[C:32]([CH:34]=O)[N:33]=2)[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26]>C1COCC1.C(OCC)(=O)C>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:29]2[S:30][CH:31]=[C:32]([CH:34]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:33]=2)[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26]

Participants

6

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 18408502HCID 18408502, compound

Product 1

HCID 67526446HCID 67526446, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

THF (5 mL) was added to sodium hydride (55% dispersion in mineral oil, 162 mg) under an argon atmosphere, and a solution of ethyl diethylphosphonoacetate (832 mg) in THF (2 mL) was added dropwise to the mixture at −10° C. After 30 minutes, a solution of 2-(3,4,5-trimethoxyphenyl)thiazole-4-carboaldehyde (942 mg) in THF (8 mL) was slowly added to the resultant mixture, and the mixture was warmed to room temperature over 30 minutes and then stirred for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, dried over anhydrous sodium sulfate. After concentrating the reaction mixture under reduced pressure, the resultant crude crystals were recrystallized from ethyl acetate-hexane to obtain the title compound.

Workup

  1. washwashed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationAfter concentrating the reaction mixture under reduced pressure
  4. customthe resultant crude crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c6c4e6e2674e4360b7613ad5213f3c47
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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