Water → HCID 12387502, compound

HRID 1497004Notes

Reaction equation

HRID 1497004 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH2:8]P(OCC)(OCC)=O)=[O:7].[CH:17](=O)/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>O1CCCC1>[C:6]([O:5][CH2:4][CH3:3])(=[O:7])/[CH:8]=[CH:17]/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 5283345(2E)-2-Decenal

Product 1

HCID 12387502HCID 12387502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% wt., 3.11 g) was suspended in dry tetrahydrofuran (200 ml) and cooled to 0° C. O,O-Diethyl ethoxycarbonylmethyl phosphonate (15.43 ml) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min and cooled to −78° C. after which (E)-dec-2-enal (11.90 ml) was added dropwise. Stirring was continued at this temperature for 2 h, after which the mixture was warmed to room temperature. The reaction mixture was poured into water, and the aqueous phase was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography.

Workup

  1. additionwas added dropwise
  2. stirringStirring
  3. waitwas continued at this temperature for 2 h
  4. temperatureafter which the mixture was warmed to room temperature
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was evaporated
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-0bcd2b0918dc493d874f2d18864c700a
Source dataset
uspto-grants-2015_12
Patent number
US09199948B2

Reaction notes

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