Potassium Carbonate → HCID 58399414, compound

HRID 1802530Notes

Reaction equation

HRID 1802530 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([CH:20]=O)[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].CC(C)C(=O)C(P(=O)([O-])[O-])=[N+]=[N-]>CO>[CH2:1]([O:8][CH2:9][C:10]1([C:20]#[CH:22])[CH2:11][CH2:12][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:18][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 58399448HCID 58399448, compoundHCID 86586111Dimethyl-1-diazo-2-oxopropylphosphonate

Product 1

HCID 58399414HCID 58399414, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-(benzyloxymethyl)-1,4-dioxaspiro[4.5]decane-8-carbaldehyde (Reference Example 86) (100 mg, 0.344 mmol) in methanol (5.2 mL), potassium carbonate (143 mg, 1.03 mmol) and dimethyl-1-diazo-2-oxopropylphosphonate (165 mg, 0.861 mmol) were added with stirring under ice-cooling, and the obtained solution was stirred at room temperature for 1 hour. The reaction was quenched by adding water to the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (88.9 mg, 0.310 mmol, 90%) as a colorless oily compound.

Workup

  1. temperaturecooling
  2. stirringthe obtained solution was stirred at room temperature for 1 hour
  3. customThe reaction was quenched
  4. additionby adding water to the reaction solution
  5. extractionthe resulting solution was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9184cc5cce6e4badaca185d002c559f1
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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