Hydrochloric Acid → HCID 68864647, compound

HRID 1454764Notes

Reaction equation

HRID 1454764 reaction equation
[Li+].[CH3:2]C([N-]C(C)C)C.[C:9]([C:12]12[CH2:21][CH:16]([C:17]([CH3:20])=[CH:18][CH2:19]1)[C:15](=[O:22])[CH2:14][CH:13]2[CH3:23])([CH3:11])=[CH2:10].CI.Cl>C1COCC1.CCCCCC.CC(OC)(C)C>[C:9]([C:12]12[CH2:21][CH:16]([C:17]([CH3:20])=[CH:18][CH2:19]1)[C:15](=[O:22])[CH:14]([CH3:2])[CH:13]2[CH3:23])([CH3:11])=[CH2:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 68526884HCID 68526884, compound

Product 1

HCID 68864647HCID 68864647, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21982663Methyl t-butylether hexaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 15.3 ml of a soln. of LDA (2M in THF/heptane/ethylbenzene, 31 mmol, 2.5 eq.) was treated dropwise with a soln. of 2.5 g of 5-Isopropenyl-4,8-dimethylbicyclo[3.3.1]non-7-en-2-one (12 mmol) in 25 ml THF. The reaction mixture was stirred 1.5 h at 0° C., treated with 2.6 ml methyl iodide (41.7 mmol, 3.4 eq.), stirred at 25° C. for 3 h, and poured into 1M aq. HCl soln. Extraction with MTBE (2×80 ml), washing of the org. phase with H2O, aq. sat. NaCl soln., drying (MgSO4) gave 3.6 g crude. FC (hexane/MTBE 24:1) gave 0.56 g (21%) of compound 3. The boiling point of the end product is 120° C. at 0.08 mbar. Rf (hexane/MTBE 24:1) 0.26.

Workup

  1. customAt 0° C.
  2. stirringstirred at 25° C. for 3 h
  3. extractionExtraction with MTBE (2×80 ml)
  4. washwashing of the org
  5. dry with material, drying (MgSO4)
  6. customgave 3.6 g crude

Sources & evidence

ORD record
ord-9a98fabd647b4798b806ae7720921054
Source dataset
uspto-grants-2009_01
Patent number
US07482313B2

Reaction notes

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