Sodium hydride → HCID 70869427, compound

HRID 1913586Notes

Reaction equation

HRID 1913586 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7]P(OCC)(OCC)=O)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:19]([O:26][C:27]([C:29]1[S:30][C:31]([CH:35]=O)=[C:32]([CH3:34])[CH:33]=1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[C:1]([O:5][C:6](=[O:16])/[CH:7]=[CH:35]/[C:31]1[S:30][C:29]([C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:28])=[CH:33][C:32]=1[CH3:34])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 86673329HCID 86673329, compound

Product 1

HCID 70869427HCID 70869427, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of diethylphosphonoacetic acid tert-butyl ester (0.44 g, 1.74 mmol) in tetrahydrofuran (3 ml) was added dropwise to a suspension of 60% sodium hydride (0.055 g, 1.38 mmol) in tetrahydrofuran (15 mL) with stirring at 0° C. After stirring at room temperature for 30 minutes, a solution of 5-formyl-4-methylthiophene-2-carboxylic acid benzyl ester (0.3 g, 1.15 mmol) obtained in step 2 in tetrahydrofuran (3 mL) was added dropwise at 0° C. After stirring at room temperature for 2 hours, the mixture was worked up according to a conventional method, and purified by silica gel column chromatography to give the title compound (0.35 g).

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. stirringAfter stirring at room temperature for 2 hours
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-981cb480e1da4324b9ac9bc1f04283c3
Source dataset
uspto-grants-2013_12
Patent number
US08609715B2

Reaction notes

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