Potassium Carbonate → HCID 57517507, compound

HRID 2368127Notes

Reaction equation

HRID 2368127 reaction equation
[Si:1]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([CH:25]=O)[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[C:29](P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])[O-].[K+].[K+]>CO>[C:14]([Si:1]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]#[CH:29])[CH2:21][CH2:20]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57517506HCID 57517506, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 57517507HCID 57517507, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 4-{[tert-butyl(diphenyl)silyl]oxy}cyclohexanecarbaldehyde (4.74 g), dimethyl (1-diazo-2-oxopropyl)phosphonate (2.98 g) and potassium carbonate (3.57 g) in methanol (40 mL) was stirred at room temperature for 2 hr. The reaction mixture was extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (4.15 g).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate and water
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0f1e6eb8d30046b89f68286e68fec8ba
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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