Water → HCID 10966372, compound

HRID 1844239Notes

Reaction equation

HRID 1844239 reaction equation
CC([O-:5])(C)C.[K+].[CH2:7]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)[CH:8]=[CH2:9].O.[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1>>[CH2:7]([O:10][C:11]1[CH:18]=[CH:17][C:14](/[CH:15]=[CH:21]/[C:22]([O:23][CH2:24][CH3:20])=[O:5])=[CH:13][CH:12]=1)[CH:8]=[CH2:9]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 959424-(Allyloxy)benzaldehyde2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 10966372HCID 10966372, compoundYield 90%

Conditions

Temperature
0 °C

Procedure

t-BuOK (4.57 g, 40.7 mmol) was added in small portions to a solution of triethyl phosphonoacetate (8.10 mL, 40.7 mmol) and 4-(allyloxy)benzaldehyde (Intermediate D, 6.00 g, 37.0 mmol) in THF (100 mL) cooled at 0° C., leading to the formation of a viscous mixture. After 30 min, water (20 mL) was added and the solvent was removed by rotatory evaporation. The crude residue was dissolved in EtOAc (100 mL) and washed with water (2×100 mL); the organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residue was purified by column chromatography on silica gel (7% EtOAc/Hexanes), affording 7.76 g of (E)-ethyl 3-(4-(allyloxy)phenyl)acrylate [Rf=0.4 (10% EtOAc/Hexanes), colorless oil, 90% yield].

Workup

  1. customthe solvent was removed by rotatory evaporation
  2. dissolutionThe crude residue was dissolved in EtOAc (100 mL)
  3. washwashed with water (2×100 mL)
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customAfter removal of the solvent
  7. customthe residue was purified by column chromatography on silica gel (7% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-bdd8062085ef402d99c708bdaaf75ccf
Source dataset
uspto-grants-2015_02
Patent number
US08946296B2

Reaction notes

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