Bicyclo(2.2.1)heptan-2-one → HCID 58095615, compound

HRID 1669643Notes

Reaction equation

I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:17]1[CH:21]2[CH2:22][C:23](=[O:24])[CH:19]([CH2:20]2)[CH2:18]1.[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[OH:24][C:23]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)[CH2:22][CH:21]2[CH2:20][CH:19]1[CH2:18][CH2:17]2

Participants

Conditions

Temperature: -47 °C

Procedure

A solution of methyl 4-iodobenzoate (23.1 g, 0.0882 mol) dissolved in anhydrous THF (200 mL) was cooled to −47° C. Isopropyl magnesium chloride (48 mL of a 2.0 M solution in THF, 0.097 mol) was slowly added to the solution. The reaction mixture was stirred at −47° C. for 1 h, then cannulated into a pre-cooled solution of norcamphor (11.6 g, 0.105 mol) in THF (100 mL) at −47° C. The reaction mixture was subsequently stirred at −40° C. overnight, and was then allowed to warm to −20° C. Saturated aqueous ammonium chloride was added. EtOAc was used to extract three times. The combined organic portion was washed with water and brine, dried (MgSO4), filtered, concentrated, and purified by flash chromatography on silica gel (gradient elution; 0%-30% EtOAc/hexanes as eluent) to afford the title compound.

Workup

stirringThe reaction mixture was subsequently stirred at −40° C. overnight
temperatureto warm to −20° C
extractionto extract three times
washThe combined organic portion was washed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
custompurified by flash chromatography on silica gel (gradient elution; 0%-30% EtOAc/hexanes as eluent)

Sources & evidence

ORD record: ord-4cce7d41d42e482584410299fa5527f2
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989472B2

Reaction notes

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