tert-Butyl (triphenylphosphoranylidene) acetate → HCID 58105211, compound

HRID 1668527Notes

Reaction equation

HRID 1668527 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=1.[C:11]([O:15][C:16]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C=O)C>[OH:10][CH2:9][C:7]1[N:8]=[C:3](/[CH:2]=[CH:18]/[C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH:4]=[CH:5][CH:6]=1.[OH:10][CH2:9][C:7]1[N:8]=[C:3](/[CH:2]=[CH:18]\[C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 121863846-(Hydroxymethyl)pyridine-2-carbaldehyde

Product 2

HCID 58105211HCID 58105211, compoundHCID 66852435HCID 66852435, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Hydroxymethylpyridine-2-carbaldehyde (15.3 g) was dissolved in 250 mL of dry DMF, and 50 g of (t-butoxycarbonylmethylene)triphenylphosphorane was added to the above solution, and then the mixture was stirred at room temperature for 30 minutes. The reaction mixture was thrown into ice-water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added 300 mL of a mixture of hexane-ethyl acetate (2:1), the insoluble portion was filtrated off. The filtrate was concentrated under reduced pressure, the residue was purified by chromatography on silica gel (hexane-ethyl acetate=2:1) to give 16.86 g of t-butyl 3-(6-hydroxymethylpyridin-2-yl)-trans-acrylate and 5.69 g of t-butyl 3-(6-hydroxymethylpyridin-2-yl)-cis-acrylate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added 300 mL of a mixture of hexane-ethyl acetate (2:1)
  6. filtrationthe insoluble portion was filtrated off
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by chromatography on silica gel (hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-6d38de9f3b2b4d20af1005030a16d519
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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