Triethyl phosphonoacetate → Ethyl 3-(5,6,7-trimethoxynaphthalen-2-yl)propenoate

HRID 720313Notes

Reaction equation

HRID 720313 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][O:18][C:19]1[C:28]([O:29][CH3:30])=[C:27]([O:31][CH3:32])[CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23]([CH:33]=O)=[CH:24]2>C1COCC1.C(OCC)(=O)C>[CH3:17][O:18][C:19]1[C:28]([O:29][CH3:30])=[C:27]([O:31][CH3:32])[CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23]([CH:33]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:24]2

Participants

6

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 218916375,6,7-Trimethoxynaphthalene-2-carbaldehyde

Product 1

HCID 68436859Ethyl 3-(5,6,7-trimethoxynaphthalen-2-yl)propenoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

55% Sodium hydride (241 mg) was suspended in THF (2.5 mL) at −10° C. under an argon atmosphere, a solution of ethyl diethylphosphonoacetate (1.23 g) in THF (5 mL) was added dropwise to the suspension, and the mixture was stirred for 30 minutes. A solution of 5,6,7-trimethoxynaphthalene-2-carboaldehyde (1.23 g) in THF (10 mL) was then added dropwise, and the mixture was stirred for 30 minutes at −10° C. and 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate, washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to obtain the title compound.

Workup

  1. stirringthe mixture was stirred for 30 minutes at −10° C. and 1 hour at room temperature
  2. washwashed with 2 M hydrochloric acid, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-09db1d04b4fb45d4926a8b44684d8d97
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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