Potassium Carbonate → HCID 82810771, compound

HRID 404216Notes

Reaction equation

HRID 404216 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CC(C)C(=O)C(P(=O)([O-])[O-])=[N+]=[N-].[F:19][C:20]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O>CO>[C:22]([C:21]1[CH:24]=[CH:25][CH:26]=[C:27]([O:28][CH3:29])[C:20]=1[F:19])#[CH:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 37744632-Fluoro-3-methoxybenzaldehydeHCID 86586111Dimethyl-1-diazo-2-oxopropylphosphonate

Product 1

HCID 82810771HCID 82810771, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (3.6 g, 26.0 mmol) and dimethyl-1-diazo-2-oxopropylphosphonate (2.4 mL, 15.6 mmol) were added sequentially to a solution of 2-fluoro-3-methoxybenzaldehyde (2.0 g, 13.0 mmol) in methanol (100 mL), and the reaction was allowed to stir at room temperature for 16 h. After concentrating the reaction mixture under reduced pressure, the crude material was purified by flash chromatography (40 g silica gel column, 0-40% gradient ethyl acetate in hexanes) to provide a clear colorless oil (1.8 g, 92%). MS (GCMS) m/z 150. 1H NMR (400 MHz, CHLOROFORM-d) δ3.31 (d, J=0.78 Hz, 1H) 3.90 (s, 3H) 6.93-7.11 (m, 3H).

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure
  2. customthe crude material was purified by flash chromatography (40 g silica gel column, 0-40% gradient ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0ee9c85b54f14a6d9bf2444ee02b6e73
Source dataset
uspto-grants-2014_06
Patent number
US08748466B2

Reaction notes

Loading…