Potassium Carbonate → HCID 58124849, compound

HRID 1971699Notes

Reaction equation

HRID 1971699 reaction equation
[CH3:1][N:2]([C:10]([CH3:16])([CH2:12][CH2:13][CH:14]=O)[CH3:11])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[N+](=[C:19](P(=O)(OC)OC)C(=O)C)=[N-].C([O-])([O-])=O.[K+].[K+]>CO.O>[CH3:1][N:2]([C:10]([CH3:16])([CH2:12][CH2:13][C:14]#[CH:19])[CH3:11])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 58124919HCID 58124919, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 58124849HCID 58124849, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 150 mg of 12e in 3 ml of methanol was added 250 mg of dimethyl 1-diazo-2-oxopropylphosphonate and 250 mg of K2CO3. The mixture was stirred at RT overnight. Then reaction was diluted with water and the product was extracted with ether. The extract was washed once with sat. NaCl, dried, concentrated and filtered over a short silica column, using a pentane-ether gradient as eluent, to give 130 mg of 12f as colorless oil; Rf 0.55 (heptane/ether 3/1). NMR (CDCl3) δ 1.33 (s, 3, 2×CH3), 1.48 (s, 9, tertC4H9), 1.92 (t, 1, acetylene-H), 2.10 (m, 4, CH2CH2), 2.88 (s, 3, NCH3).

Workup

  1. customThen reaction
  2. extractionthe product was extracted with ether
  3. washThe extract was washed once with sat. NaCl
  4. customdried
  5. concentrationconcentrated
  6. filtrationfiltered over a short silica column

Sources & evidence

ORD record
ord-a229cd10ce0f4ce38d2355defeea7fed
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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