Sodium hydride → HCID 66991737, compound

HRID 556284Notes

Reaction equation

HRID 556284 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH:11]=[CH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:7][C:4]=1[CH:5]=O.C(OP([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(OCC)=O)C.[H-].[Na+]>C1COCC1>[C:33]([O:32][C:30](=[O:31])[CH:29]=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([CH:11]=[CH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:3]=1[O:2][CH3:1])([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 86619746HCID 86619746, compound

Product 1

HCID 66991737HCID 66991737, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-methoxy-4-(3-oxo-3-phenyl-propenyl)-benzaldehyde (550 mg, 2.07 mmol) was dissolved in THF (5 ml) and the resulting solution was added to a stirring mixture of tert-butyl diethylphosphonoacetate (603 mg, 2.27 mmol) and NaH (107 mg, 2.69 mmol, 60% oil dispersion) in THF (5 ml). After 15 minutes the reaction was quenched by the addition of water and partitioned between water and EtOAc. The organic extract was dried over Na2SO4 and evaporated under vacuo giving a crude that was purified by silica gel chromatography (EtOAc/petroleum ether 1:6). The collected fraction gave 635 mg of 3-[2-methoxy-4-(3-oxo-3-phenyl-propenyl)-phenyl]-acrylic acid tert-butyl ester as a yellow oil.

Workup

  1. customAfter 15 minutes the reaction was quenched by the addition of water
  2. custompartitioned between water and EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. customevaporated under vacuo
  6. customgiving a crude that
  7. customwas purified by silica gel chromatography (EtOAc/petroleum ether 1:6)

Sources & evidence

ORD record
ord-c47d5252913243d3b0723fe9cc085630
Source dataset
uspto-grants-2011_11
Patent number
US08058273B2

Reaction notes

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