Potassium Carbonate → HCID 58124895, compound

HRID 1971717Notes

Reaction equation

HRID 1971717 reaction equation
[C:1]([N:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=O)[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[C:20]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-].[NH4+].[Cl-]>CO>[C:1]([N:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[CH:20])[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 58124943HCID 58124943, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 58124895HCID 58124895, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 850 mg of 16g in 12 ml of methanol was added 850 mg of K2CO3, followed at 0° C. by 850 mg of dimethyl 1-diazo-2-oxopropylphosphonate. The mixture was stirred at 0° C. for 2 hr, followed by stirring at RT for 16 hr. The reaction mixture was poured into 5% aq. NH4Cl solution and extracted with ethyl acetate. The extract was washed with water, dried, concentrated and the crude material was purified by chromatography over silica gel, using a gradient of heptane/ethyl acetate as eluent, to give 650 mg of 16h as a colorless oil, as the methyl ester (due to transesterfication in the medium).

Workup

  1. stirringby stirring at RT for 16 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe crude material was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-7d901e5f671949ec8a34d4fd9130c2cf
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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