Water → HCID 54420533, compound

HRID 1646227Notes

Reaction equation

HRID 1646227 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27].O>O1CCCC1>[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[CH:7][C:5]([O:4][CH3:3])=[O:6])=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 19801846HCID 19801846, compound

Product 1

HCID 54420533HCID 54420533, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a current of argon, a solution having 832 mg of sodium hydride suspended in 60 ml and a solution of 4.17 g of trimethyl phosphonoacetate in 15 ml of tetrahydrofuran added thereto as kept cooled with ice were stirred for 30 minutes and the resultant mixture and a solution of 4.39 g of 4-methoxymethoxy-3-nitrobenzaldehyde in 15 ml of tetrahydrofuran added thereto were stirred for eight hours with the temperature raised to room temperature in the meantime. The produced reaction mixture was combined with water and extracted from ethyl acetate. The consequently separated organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The residue from drying was concentrated under a vacuum. The resultant concentrate was subjected to silica gel column chromatography. From the hexane-ethyl acetate (3:1 V/V) eluate, 4.52 g of methyl 4-methoxymethoxy-3-nitrocinnamate was obtained in the form of yellow crystals. The yield was 81%.

Workup

  1. temperatureas kept cooled with ice
  2. stirringthereto were stirred for eight hours with the temperature
  3. customThe produced reaction mixture
  4. extractionextracted from ethyl acetate
  5. washThe consequently separated organic layer was washed with saturated saline solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe residue from drying
  8. concentrationwas concentrated under a vacuum
  9. concentrationThe resultant concentrate

Sources & evidence

ORD record
ord-c27a1e5ceb2e4f14b4444dbe8b030219
Source dataset
uspto-grants-1993_01
Patent number
US05179105

Reaction notes

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