Tetrahydrofuran → HCID 59252318, compound

HRID 2265903Notes

Reaction equation

HRID 2265903 reaction equation
C[C:2](P(OC)(O)=O)([C:4]([O-:6])=[O:5])[CH3:3].[H-].[Na+].[CH:14]([O:17][CH:18]1[CH2:23][CH2:22]C(=O)[CH2:20][CH2:19]1)([CH3:16])[CH3:15].[CH2:25]1COCC1>>[CH3:25][O:6][C:4](=[O:5])[CH:2]=[C:3]1[CH2:22][CH2:23][CH:18]([O:17][CH:14]([CH3:16])[CH3:15])[CH2:19][CH2:20]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 184137284-[(Propan-2-yl)oxy]cyclohexan-1-oneHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 59252318HCID 59252318, compoundYield 74%

Conditions

Temperature
2.5 °C

Procedure

Trimethylphosphonoacetate (700 mg, 3.87 mmol) was solved in 10 ml of THF and added into a cold (0-5° C.) mixture of sodium hydride (169 mg, 3.87 mmol, 55%) in 10 ml THF. After 1 hour stirring at 0-5° C. 4-isopropoxy-cyclohexanone (550 mg, 3.5 mmol) in 5 ml THF was added drop wise. The reaction mixture was quenched after 1 hour at room temperature with saturated NaHCO3-solution and extracted two times with ethyl acetate. The organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product was purified with column chromatography on silica gel using heptane:ethyl acetate 90:10->20:80. The product fractions were concentrated to give 550 mg (74% yield) of a colorless liquid. MS (m/e): 213.3 (M+H+).

Workup

  1. customThe reaction mixture was quenched after 1 hour at room temperature with saturated NaHCO3-solution
  2. extractionextracted two times with ethyl acetate
  3. washThe organic extracts were washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified with column chromatography on silica gel
  8. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-33c5e72f61a54e0a9aa15feb77ef5d1d
Source dataset
uspto-grants-2010_12
Patent number
US07858630B2

Reaction notes

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