Diethyl Ether → HCID 68864848, compound

HRID 1454767Notes

Reaction equation

HRID 1454767 reaction equation
[C:1]([C:4]12[CH2:13][CH:8]([C:9]([CH3:12])=[CH:10][CH2:11]1)[C:7](=[O:14])[CH2:6][CH:5]2[CH3:15])([CH3:3])=[CH2:2].[Li]C.[CH3:18]COCC.[NH4+].[Cl-]>C1COCC1>[C:1]([C:4]12[CH2:13][CH:8]([C:9]([CH3:12])=[CH:10][CH2:11]1)[C:7]([CH3:18])([OH:14])[CH2:6][CH:5]2[CH3:15])([CH3:3])=[CH2:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 68526884HCID 68526884, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 68864848HCID 68864848, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

At 5° C., a soln. of 1 g of 5-isopropenyl-4,8-dimethylbicyclo[3.3.1]non-7-en-2-one (4.9 mmol) in 15 ml THF was treated dropwise with 21 ml 1.4M MeLi in Et2O (29.4 mmol, 6 eq.). The reaction mixture was stirred 5 h at 5° C., warmed to 25° C. overnight, poured into aq. sat. NH4Cl soln., and extracted with Et2O. The org. phase was washed with aq. sat. NaCl soln., dried, and concentrated. FC (SiO2, hexane/Et2O 9:1) of the crude (1.2 g, starting material/OH exo/OH endo 17:65:18)gave 0.2 g of starting material (20%), 0.5 g 8A (46%), 0.25 g 8A/8B (1:1, 23%), and 0.1 g 8B (9%).

Workup

  1. customAt 5° C.
  2. temperaturewarmed to 25° C. overnight
  3. extraction, and extracted with Et2O
  4. washphase was washed with aq. sat. NaCl soln
  5. custom, dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0a6182fe3de494aa77efb94b993ef13
Source dataset
uspto-grants-2009_01
Patent number
US07482313B2

Reaction notes

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