Tetrahydrofuran → HCID 25008219, compound

HRID 1925673Notes

Reaction equation

HRID 1925673 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[CH3:7])=[O:5].[H-].[Na+].[CH:18](=O)/[CH:19]=[CH:20]/[CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34]C.[NH4+].[Cl-].[CH2:39]1COCC1>>[CH3:39]/[C:6](=[CH:7]\[CH:34]=[CH:33]\[CH2:32][CH2:31]/[CH:30]=[CH:29]\[CH2:28]/[CH:27]=[CH:26]\[CH2:25]/[CH:24]=[CH:23]\[CH2:22]/[CH:21]=[CH:20]\[CH2:19][CH3:18])/[C:4]([O:3][CH2:2][CH3:1])=[O:5]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 107155Triethyl 2-phosphonopropionateHCID 71501098HCID 71501098, compound

Product 1

HCID 25008219HCID 25008219, compound

Conditions

Temperature
-40 °C

Procedure

Triethyl 2-phosphonopropionate (458 μl, 2.13 mmol) was added to a suspension of sodium hydride (88 mg, 60% dispersion in mineral oil, 2.2 mmol) in dry THF (6 ml) at 0° C. After 50 minutes at 0° C. the mixture was cooled to −40° C. and (2E,6Z,9Z,12Z,15Z)-octadeca-2,6,9,12,15-pentaenal (500 mg, 1.94 mmol) in THF (1 ml) was added. The mixture was stirred for 60 minutes at −40° C. to −20° C. A saturated aqueous NH4Cl solution of was added and the phases were separated. The aqueous phase was extracted with diethylether. The combined organic phases were washed with brine, water and dried (MgSO4). Evaporation of the solvents under reduced pressure gave the ester 10.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with diethylether
  3. washThe combined organic phases were washed with brine, water
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-40fd95be526b4fe4b93f54643be93124
Source dataset
uspto-grants-2012_05
Patent number
US08178708B2

Reaction notes

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