Water → Diethyl 2-benzyloxymethyl-2-cyclohexylmalonate

HRID 129270Notes

Reaction equation

HRID 129270 reaction equation
[CH:1]1([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>O1CCCC1>[CH2:23]([O:22][CH2:21][C:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 240541Diethyl 2-cyclohexylmalonate

Product 1

HCID 19373401Diethyl 2-benzyloxymethyl-2-cyclohexylmalonateYield 107.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl cyclohexylmalonate (18.7 g) (ref. Bailstein 9, 739) was added to a stirred suspension of sodium hydride (4.8 g., 50% dispersion in oil) in dry tetrahydrofuran (50 ml) under nitrogen. The mixture was refluxed, with stirring, for one hour. The mixture was cooled and benzyl chloromethyl ether (13.9 g.) (Sigma Chemical Company) in dry tetrahydrofuran (50 ml) was added and the mixture was refluxed, with stirring, for three hours. The mixture was cooled and poured into water. The aqueous mixture was extracted with ether. The ether extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. Diethyl 2-benzyloxymethyl-2cyclohexylmalonate (30 g.) was obtained as a brown oil and was used without further purification.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureThe mixture was cooled
  3. temperaturethe mixture was refluxed
  4. stirringwith stirring, for three hours
  5. temperatureThe mixture was cooled
  6. extractionThe aqueous mixture was extracted with ether
  7. washThe ether extracts were washed with water
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-38a6dfd2e9fe466dad6bdb73c2880ae9
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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