Triethyl phosphonoacetate → HCID 18349870, compound

HRID 2392938Notes

Reaction equation

HRID 2392938 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6]P(OCC)(OCC)=O)=[O:5].CC([O-])(C)C.[K+].[CH3:21][C:22]1([CH3:37])[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[C:28]2[CH:27]=[C:26]([C:34](=O)[CH3:35])[CH:25]=[CH:24][C:23]1=2>C1COCC1>[CH2:2]([O:3][C:4](=[O:5])/[CH:6]=[C:34](/[C:26]1[CH:25]=[CH:24][C:23]2[C:22]([CH3:37])([CH3:21])[CH2:31][CH2:30][C:29]([CH3:32])([CH3:33])[C:28]=2[CH:27]=1)\[CH3:35])[CH3:1]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 18349870HCID 18349870, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7.30 ml of phosphonoacetic acid triethyl ester were dissolved in 100 ml of abs. THF. 3.90 g of KOtBu were added at 0° C. and the mixture stirred for 15 minutes at this temperature. 4.20 g of 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone, dissolved in 30 ml of THF, were added dropwise within 30 minutes at room temperature and stirring continued at 40° C. for 16 hours. The reaction mixture was then poured onto crashed ice/NH4Cl, extracted with EtOEt, washed with brine and H2O, and dried over Na2 SO4. Evaporation of the solvent, followed by flash chromatography (silica gel, hexane/AcOEt=97:3) yielded 3.70 g of (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enoic acid ethyl ester as yellowish oil (GC-purity 98%).

Workup

  1. additionwere added dropwise within 30 minutes at room temperature
  2. stirringstirring
  3. waitcontinued at 40° C. for 16 hours
  4. additionThe reaction mixture was then poured
  5. extractionextracted with EtOEt
  6. washwashed with brine and H2O
  7. customdried over Na2 SO4
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b02671f3da254a0eabe7e6734eb937c8
Source dataset
uspto-grants-1998_09
Patent number
US05801253

Reaction notes

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