Triethyl phosphonoacetate → HCID 10335194, compound

HRID 742310Notes

Reaction equation

HRID 742310 reaction equation
[C:1]([C:5]1[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:7][CH:6]=1)(=O)[CH2:2][CH3:3].CC(C)([O-])C.[K+].C(OP([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])(OCC)=O)C.[Cl-].[NH4+]>O1CCCC1>[CH2:2](/[C:1](/[C:5]1[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:7][CH:6]=1)=[CH:32]\[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH3:3]

Participants

6

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 25517Ammonium ChlorideHCID 14226991Tert-butyl 4-propionylbenzoate2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 10335194HCID 10335194, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The ketone thus prepared was subjected to the Horner-Emmons reaction. That is, potassium t-butoxide (19 g) was added to a solution of ethyl diethylphosphonoacetate (36 ml) in tetrahydrofuran (400 ml). The obtained mixture was stirred at room temperature for 30 minutes, followed by the addition of a solution of the above ketone (21.1 g) in tetrahydrofuran (40 ml). The obtained mixture was stirred at 55° to 65° C. for 1.5 hours to complete a reaction. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride to give 22.7 g of t-butyl 4-(1-ethyl-2-ethoxycarbonyl-E-ethenyl)benzoate.

Workup

  1. customwas subjected to the Horner-Emmons reaction
  2. stirringThe obtained mixture was stirred at 55° to 65° C. for 1.5 hours
  3. customa reaction

Sources & evidence

ORD record
ord-38768816d61347bb93e9519f10092d55
Source dataset
uspto-grants-1996_09
Patent number
US05554615

Reaction notes

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