Triethyl phosphonoacetate → HCID 18349870, compound

HRID 2229242Notes

Reaction equation

HRID 2229242 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([CH3:15])([CH3:14])[CH2:9][CH2:8][C:7]2([CH3:17])[CH3:16])(=O)[CH3:2].[H-].[Na+].C(OP([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])(OCC)=O)C>C1COCC1>[CH3:14][C:10]1([CH3:15])[CH2:9][CH2:8][C:7]([CH3:17])([CH3:16])[C:6]2[CH:5]=[C:4](/[C:1](/[CH3:2])=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:13]=[CH:12][C:11]1=2

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

Product 1

HCID 18349870HCID 18349870, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Acetyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (5.07 g) was added to a cooled (0° C.) mixture of NaH (60% oil dispersion, 1.10 g) and ethyl diethylphosphonoacetate (6.49 g) in THF (50 ml). The mixture was stirred at room temperature for 14 hours. The reaction was quenched by the addition of water and the mixture was diluted with ethyl acetate. The organic layer was washed with water and brine, dried and concentrated to give the titled compound (6.50 g) as a colorless oil.

Workup

  1. temperaturea cooled
  2. customThe reaction was quenched by the addition of water
  3. additionthe mixture was diluted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0ffebf8c8e064f28bcbda39540f3d5e7
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

Loading…