Triethyl phosphonoacetate → HCID 86758349, compound

HRID 2229244

Reaction equation

HRID 2229244 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:14])[CH:10]=2)[CH:5]=1)(=O)[CH3:2].[H-].[Na+].C(OP([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])(OCC)=O)C>C1COCC1>[CH3:14][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]=[C:4](/[C:1](/[CH3:2])=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 5980856'-Methyl-2'-acetonaphthone

Product 1

HCID 86758349HCID 86758349, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Acetyl-6-methylnaphthalene (5.08 g) was added to a cooled (0° C.) mixture of NaH (60% oil dispersion, 2.34 g) in THF (150 ml) and ethyl diethylphosphonoacetate (14.12 g) and the mixture was stirred at room temperature for 14 hours. The reaction was quenched by the addition of water. The organic layer was washed with water and brine, dried and concentrated. Recrystallization of the residue from hexane gave the titled compound (3.25 g) as a colorless solid.

Workup

  1. temperaturea cooled
  2. customThe reaction was quenched by the addition of water
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customRecrystallization of the residue from hexane

Sources & evidence

ORD record
ord-ea51eea4cc4c4c3995ef2fc70dde01a7
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Linked notes

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