Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 12872207, compound

HRID 1011034Notes

Reaction equation

HRID 1011034 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]=[C:3]([CH:7]=O)[CH2:2]1.[C:9]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:11][CH2:12][CH3:13])=[O:10]>ClCCl>[O:1]1[CH2:6][CH2:5][CH:4]=[C:3](/[CH:7]=[CH:14]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2]1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 834235,6-Dihydro-2H-pyran-3-carbaldehyde

Product 1

HCID 12872207HCID 12872207, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 5,6-dihydro-2H-pyran-3-carbaldehyde (5.0 g) in dry dichloromethane (150 ml) at 0° C., was added carbethoxymethylene-triphenylphosphorane (15.53 g). The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with dichloromethane (150 ml) and washed with water (150 ml) and a saturated aqueous solution of brine (150 ml). The organic layer was dried by passing through a hydrophobic frit and concentrated in vacuo. to afford a yellow oil. The product was purified by silica chromatography (120 g) (ISCO) using a gradient elution of 0-10% cyclohexane:ethyl acetate to afford the title compound as a clear oil (5.59 g).

Workup

  1. washwashed with water (150 ml)
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. customto afford a yellow oil
  5. customThe product was purified by silica chromatography (120 g) (ISCO)
  6. washa gradient elution of 0-10% cyclohexane

Sources & evidence

ORD record
ord-0645d213d79b474fadf238e2cb46f48c
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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