Trimethyl phosphonoacetate → HCID 54096970, compound

HRID 1980865Notes

Reaction equation

HRID 1980865 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].CC(C)([O-])C.[K+].[CH:18]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[C:26]=1[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)=O>C1COCC1>[CH3:1][O:2][C:3]([CH:5]=[CH:18][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[C:26]=1[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)=[O:4]

Participants

5

Reactant 3

HCID 80029Trimethyl phosphonoacetateHCID 20400820HCID 20400820, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54096970HCID 54096970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Trimethyl phosphonoacetate (328 mg) is added dropwise to a solution of potassium tert-butoxide (220 mg) in THF (5 ml) of 0° under a nitrogen atmosphere. The solution is stirred at 0° for 20 minutes, then cooled to -78°. A solution of 3-(5-formylpentyl)-2-(3-pyridyl)-1-methylindole (450 mg) in THF (5 ml) is added dropwise over 15 minutes. The mixture is kept at -78° for 15 minutes, then the cooling bath is removed. The mixture is stirred overnight at room temperature, then diluted with water (25 ml) and extracted with diethyl ether (3×25 ml). The combined extracts are washed with saturated sodium bicarbonate, then brine, and dried over anhydrous magnesium sulfate. Concentration in vacuo yields the α,β unsaturated ester, 3-(7-methoxycarbonylhept-6-enyl)-2-(3-pyridyl)-1-methylindole.

Workup

  1. temperaturecooled to -78°
  2. waitThe mixture is kept at -78° for 15 minutes
  3. customthe cooling bath is removed
  4. stirringThe mixture is stirred overnight at room temperature
  5. additiondiluted with water (25 ml)
  6. extractionextracted with diethyl ether (3×25 ml)
  7. washThe combined extracts are washed with saturated sodium bicarbonate
  8. dry with materialbrine, and dried over anhydrous magnesium sulfate
  9. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c527345a8ea642f4b1f430d311364036
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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