Sodium hydride → HCID 131726621, compound

HRID 1178562Notes

Reaction equation

HRID 1178562 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].[CH:14]1([CH2:19][C:20](=O)[CH3:21])[CH2:18][CH2:17][CH2:16][CH2:15]1>C1COCC1.[Cl-].[Na+].O>[CH:14]1([CH2:19]/[C:20](/[CH3:21])=[CH:7]/[C:5]([O:4][CH3:3])=[O:6])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 1368972-Propanone, 1-cyclopentyl-

Product 1

HCID 131726621HCID 131726621, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (956 mg, 60% in oil, 23.9 mmol) in THF (60 mL) cooled at 0° C. was added dropwise trimethyl phosphonoacetate (3.87 mL, 4.35 g, 23.9 mmol). The mixture was stirred for 20 mn at 0° C. and cyclopentylacetone (2.22 mL, 2.00 g, 15.9 mmol) was added dropwise. The solution was warmed to 25° C., then refluxed for 2 h, and poured in a solution of brine (100 mL). The reaction mixture was extracted with ethyl acetate (2×50 mL) and the combined organic phase was dried over sodium sulfate and concentrated to give the ester (2.87 g, 99%) as a mixture of E and Z isomers 3:1. MS (m/z) 182 (M).

Workup

  1. temperatureThe solution was warmed to 25° C.
  2. temperaturerefluxed for 2 h
  3. extractionThe reaction mixture was extracted with ethyl acetate (2×50 mL)
  4. dry with materialthe combined organic phase was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7bd3e7bb9c064aeca93e2e3220d7deb2
Source dataset
uspto-grants-2007_10
Patent number
US07276531B2

Reaction notes

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