Sodium hydride → HCID 117992948, compound

HRID 571132Notes

Reaction equation

HRID 571132 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4](P(OCC)(OCC)=O)[CH2:5][CH3:6].[H-].[Na+].[C:18]([O:22][C:23]([C:25]1[S:26][C:27]([CH:30]=O)=[CH:28][CH:29]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>O1CCCC1>[C:18]([O:22][C:23]([C:25]1[S:26][C:27](/[CH:30]=[C:4](/[C:3]([O:2][CH3:1])=[O:15])\[CH2:5][CH3:6])=[CH:28][CH:29]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12565589HCID 12565589, compoundHCID 21473735tert-Butyl 5-formylthiophene-2-carboxylate

Product 1

HCID 117992948HCID 117992948, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(diethylphosphono)butyric acid methyl ester (46 g, 0.193 mol) was dissolved in tetrahydrofuran (300 mL), 60% sodium hydride (6.6 g, 0.165 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(32.1 g, 0.15 mol) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 2 hours. 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 (35.6 g, 0.12 mol, 80%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  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-28d6ca671be04cecb06fed262e3d7c56
Source dataset
uspto-grants-2015_05
Patent number
US09024044B2

Reaction notes

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