Cyclopentanone → HCID 59602251, compound

HRID 1631846Notes

Reaction equation

HRID 1631846 reaction equation
C[Mg]Cl.[C:4]1(=[O:14])[C:8]2(CCCC[CH2:9]2)[CH2:7]CC1.C1(=O)CCCC1.[Cl-].[NH4+].[CH3:23][C:24]1([OH:34])[C:28]2([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:27][CH2:26][CH2:25]1>C1(C)C=CC=CC=1.O1CCCC1>[C:4]([O:34][C:24]1([CH3:23])[C:28]2([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:27][CH2:26][CH2:25]1)(=[O:14])[C:8]([CH3:9])=[CH2:7]

Participants

8

Reactant 5

HCID 8452CyclopentanoneHCID 25517Ammonium ChlorideHCID 556398Spiro[4.5]decan-1-oneHCID 59602200HCID 59602200, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 59602251HCID 59602251, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

With stirring under nitrogen atmosphere at 40° C., 500 ml of toluene was added dropwise to a tetrahydrofuran solution of 0.95 mol methylmagnesium chloride (which had been prepared from 23 g of metallic magnesium, 500 ml of tetrahydrofuran and chloromethane), and then a mixture of 73 g of spiro[4.5]decan-1-one (which had been synthesized from cyclopentanone by a method as described in A. P. Krapcho, Synthesis, 1974, p 383 and references cited therein) and 1300 ml of toluene added. The reaction mixture was stirred overnight at 70° C. and returned to room temperature, after which a saturated ammonium chloride aqueous solution was added to stop the reaction. Through ordinary work-up of extraction, washing and drying, and subsequent vacuum distillation, there was obtained 50.2 g (yield 63%) of the target compound, 1-methylspiro[4.5]decan-1-ol.

Workup

  1. customKrapcho, Synthesis, 1974, p 383 and references
  2. stirringThe reaction mixture was stirred overnight at 70° C.
  3. customreturned to room temperature
  4. customthe reaction
  5. extractionThrough ordinary work-up of extraction
  6. washwashing
  7. customdrying
  8. distillationsubsequent vacuum distillation

Sources & evidence

ORD record
ord-a68df33a20ab4fe080e3fb19eb30c7a8
Source dataset
uspto-grants-2014_07
Patent number
US08791288B2

Reaction notes

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