tert-Butyl (triphenylphosphoranylidene) acetate → HCID 66760332, compound

HRID 889211Notes

Reaction equation

HRID 889211 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)=O.C1(P(=[CH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[C:36]([O:35][C:33](=[O:34])/[CH:32]=[CH:1]/[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 586269Methyl 6-formylpyridine-3-carboxylate

Product 1

HCID 66760332HCID 66760332, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 6-formylnicotinate (1.0 g, 6.06 mmol) and tert-butyl (triphenylphosphoranylidene)acetate (2.73 g, 7.27 mmol) were put in suspension in water (50 mL) and stirred at 90° C. for 2 h. The reaction mixture was cooled to room temperature and concentrated under pressure. The residue was triturated in ethyl acetate and filtered. The filtrate was concentrated and purified by flash chromatography using hexanes-ethyl acetate 10% to give (E)-methyl 6-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)nicotinate. MS (APCI) 264 (M+). (E)-methyl 6-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)nicotinate was dissolved in ethanol in the presence of 50 mg Pd/C, 10% and stirred under hydrogen balloon overnight to give 6-2(tert-butoxycarbonyl-ethyl)nicotinic methyl ester. LCMS: 266 (M+)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under pressure
  3. customThe residue was triturated in ethyl acetate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-84bed8e4da9a4f089ca6fd05beef7d60
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

Loading…