Benzaldehyde → HCID 68565974, compound

HRID 2100475Notes

Reaction equation

HRID 2100475 reaction equation
[CH3:1][CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Br-].[C:16]1([C:22]([PH3+])=[C:23](C2C=CC=CC=2)C2C=CC=CC=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH:37](=O)C1C=CC=CC=1>C(OCC)C.C(OCC)(=O)C>[CH2:11]([O:10][C:8](=[O:9])[C:2]([CH3:37])([CH2:1][CH:23]=[CH:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:12]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 11857Diethyl methylmalonateHCID 24758Sodium hydrideHCID 56923598HCID 56923598, compound

Product 1

HCID 68565974HCID 68565974, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Under cooling (0° C.), diethyl methylmalonate ([609-08-5], 1.175 g, 7 mmol) was added to a suspension of NaH (60% in mineral oil, 325 mg, 8 mmol) in diethyl ether (30 ml). After 3 h at r.t, the solvent was evaporated and the residue was dissolved in DMF (20 ml). To this solution, triphenylvinylphosphonium bromide ([5044-52-0], 3.00 g, 8 mmol) and benzaldehyde ([100-52-7], 860 mg, 8 mmol) were added. The reaction mixture was stirred at 100° C. overnight, and was then taken up in ethyl acetate, washed (H2O), and dried (Na2SO4). The solvent was evaporated, and 2-methyl-2-(3-phenyl-allyl)-malonic acid diethyl ester was isolated from the residue by column chromatography (silica gel, ethyl acetate/heptane). MS: m/e=291.0 [M+H+].

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue was dissolved in DMF (20 ml)
  3. washwashed (H2O)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-851eba3b5c484275b878ee1db49f750f
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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