Acetone → HCID 23436664, compound

HRID 992791Notes

Reaction equation

HRID 992791 reaction equation
[CH:1]1([CH:6]2[CH2:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:8]([CH3:15])([CH3:14])[CH2:7]2)[CH:5]=[CH:4][CH:3]=[CH:2]1.CO.[CH3:18][C:19]([CH3:21])=O.N1CCCC1>C(OCC)C.O.C(O)(=O)C>[CH3:14][C:8]1([CH3:15])[CH2:9][C:10]([CH3:13])([CH3:12])[CH2:11][CH:6]([C:1]2[CH:2]=[CH:3][C:4](=[C:19]([CH3:21])[CH3:18])[CH:5]=2)[CH2:7]1

Participants

8

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 31268PyrrolidineHCID 85817686HCID 85817686, compound

Product 1

HCID 23436664HCID 23436664, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A 500 mL flask was charged with 1-(cyclopentadienyl)-3,3,5,5-tetramethylcyclohexane (11.87 g, 58.1 mmol), 100 mL methanol, acetone (30 mL, 430 mmol), and pyrrolidine (1.0 mL, 12 mmol). After stirring for 52 hours, 5 mL of acetic acid were added, along with 200 mL water and 100 mL diethyl ether. The organic layer was isolated and the aqueous layer was extracted with diethyl ether (3×50 mL). The combined organic layers were extracted with H2O (3×30 mL) and 10% aqueous NaOH (3×30 mL). The organic layer was dried over MgSO4, filtered, rotavapped, dried in vacuo, and pushed through a short column of alumina to provide the product in quantitative yield as a yellow oil. MS (GC-MS) m/z 244.4 (M+).

Workup

  1. customThe organic layer was isolated
  2. extractionthe aqueous layer was extracted with diethyl ether (3×50 mL)
  3. extractionThe combined organic layers were extracted with H2O (3×30 mL) and 10% aqueous NaOH (3×30 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customdried in vacuo
  7. customto provide the product in quantitative yield as a yellow oil

Sources & evidence

ORD record
ord-2887f5f13c4f425ab1b472cc29f6716e
Source dataset
uspto-grants-2002_10
Patent number
US06469188B1

Reaction notes

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