Ethyl Acetate → HCID 9885378, compound

HRID 1489367Notes

Reaction equation

HRID 1489367 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Si:9]([O:16][C@H:17]([CH2:23][C:24](=[O:32])[CH2:25]P(OC)(OC)=O)[CH2:18][C:19]([O:21][CH3:22])=[O:20])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(O)(C)C>[Si:9]([O:16][C@H:17]([CH2:23][C:24](=[O:32])/[CH:25]=[CH:1]/[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[CH2:18][C:19]([O:21][CH3:22])=[O:20])([C:12]([CH3:14])([CH3:13])[CH3:15])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 103713-PyridinecarboxaldehydeHCID 11430Potassium CarbonateHCID 11143440HCID 11143440, compound

Product 1

HCID 9885378HCID 9885378, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
22 °C

Procedure

In 5 mL of isopropanol (water content: 10,000 ppm) were dissolved 140 mg (1.3 mmol.) of nicotinaldehyde (pyridin-3-aldehyde) and 500 mg (1.3 mmol.) of methyl (R)-3-[(tert-butyldimethylsilyl)oxy]-6-(dimethoxyphosphinyl)-5-oxohexanoate (optical purity: 99% ee) to give an alcoholic solution. To the alcoholic solution was added 181 mg (1.3 mmol) of potassium carbonate, and the mixture was stirred for 3 hours at room temperature (22° C.). To the resulting reaction mixture was added 20 mL of ethyl acetate, and the mixture was stirred and washed with 10 mL of water. The washing was repeated twice. The organic phase was separated, dried over anhydrous magnesium sulfate, and filtered to give a filtrate. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluent:hexane/ethyl acetate=1/1, volume ratio) to give 469 mg (yield: 99%) of methyl (3R,6E)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-7-(pyridin-3-yl)-6-heptenoate.

Workup

  1. customto give an alcoholic solution
  2. customTo the resulting reaction mixture
  3. stirringthe mixture was stirred
  4. washwashed with 10 mL of water
  5. customThe organic phase was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customto give a filtrate
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-df1e90766b8d4545a973f2b2366b5b2f
Source dataset
uspto-grants-1997_10
Patent number
US05677455

Reaction notes

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