Sodium hydride → HCID 117993606, compound

HRID 587976Notes

Reaction equation

HRID 587976 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4](P(OCC)(OCC)=O)[CH3:5].[H-].[Na+].[C:17]([O:21][C:22]([C:24]1[S:25][C:26]([CH:29]=O)=[CH:27][CH:28]=1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>O1CCCC1>[C:17]([O:21][C:22]([C:24]1[S:25][C:26](/[CH:29]=[C:4](/[C:3]([O:2][CH3:1])=[O:14])\[CH3:5])=[CH:27][CH:28]=1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11401826methyl 2-(diethoxyphosphoryl)-propionateHCID 21473735tert-Butyl 5-formylthiophene-2-carboxylate

Product 1

HCID 117993606HCID 117993606, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(Diethylphosphono)propanoic acid methyl ester (23.0 g, 0.103 mol) was dissolved in tetrahydrofuran (150 mL), 60% sodium hydride (2.4 g, 0.06 mol) was added at 0° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of 5-formyl-2-thiophenecarboxylic acid tert-butyl ester obtained in Example 1, step 2 (11.0 g, 0.052 mol) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was partitioned between ethyl acetate and 1N-hydrochloric acid solution, and washed successively with water and brine. After drying over anhydrous magnesium sulfate, the residue was purified by silica gel column chromatography to give the title compound (13.1 g, 0.047 mol, 90%).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between ethyl acetate and 1N-hydrochloric acid solution
  4. washwashed successively with water and brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7b3066f429004e6d919ba3e97dfb67ef
Source dataset
uspto-grants-2016_01
Patent number
US09227949B2

Reaction notes

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