Water → HCID 12916425, compound

HRID 581709Notes

Reaction equation

HRID 581709 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10].CC([O-])(C)C.[K+].O>O1CCCC1>[CH3:13][C:8]1([C:9]([O:11][CH3:12])=[O:10])[C:1]2([CH2:5][CH2:4][CH2:3][CH2:2]2)[O:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8452CyclopentanoneHCID 28659Methyl 2-chloropropionateHCID 23665647Potassium tert-butoxide

Product 1

HCID 12916425HCID 12916425, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.3 g (0.11 mol) of cyclopentanone and 13.5 g (0.11 mol) of methyl 2-chloropropionate are cooled to 0 to 2° C.; at this temperature, 13.6 g (0.12 mol) of potassium tert-butylate suspended in 200 ml of tetrahydrofuran are added slowly dropwise with stirring over a period of about 90 minutes, after which the mixture is stirred for a further 60 minutes without cooling. A little water is added to the reaction mixture, which is subjected to extraction with diethyl ether; the organic phase is dried over sodium sulfate, the drying agent is filtered off, and evaporation of the solvent gives 10.6 g of methyl 2-methyl-1-oxaspiro[2.4]heptane-2-carboxylate, which can be employed without further purification in the subsequent stage (see b).

Workup

  1. additionare added slowly dropwise
  2. stirringafter which the mixture is stirred for a further 60 minutes
  3. temperaturewithout cooling
  4. extractionis subjected to extraction with diethyl ether
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. filtrationthe drying agent is filtered off
  7. customevaporation of the solvent

Sources & evidence

ORD record
ord-9112fb2b129e47a0bf6980c11e82861e
Source dataset
uspto-grants-1999_07
Patent number
US05922648

Reaction notes

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