Camphor, (-)- → HCID 57292197, compound

HRID 2380641Notes

Reaction equation

HRID 2380641 reaction equation
[C:1]1([Mg]Br)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:13][C@@:14]12[C:22](=[O:23])[CH2:21][C@@H:17]([C:18]1([CH3:20])[CH3:19])[CH2:16][CH2:15]2>C1COCC1>[C:1]1([C:22]2([OH:23])[CH2:21][CH:17]3[C:18]([CH3:19])([CH3:20])[C@:14]2([CH3:13])[CH2:15][CH2:16]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 444294Camphor, (-)-HCID 178418298HCID 178418298, compound

Product 1

HCID 57292197HCID 57292197, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The resulting THF solution of 1-naphthylmagnesium bromide was cooled to room temperature. Then, a THF (200 ml) solution of (-)-camphor (50 g, 0.328 mol) was added thereto, and the whole was heated under reflux for 72 hours. The reaction was terminated by cooling with ice-water and adding saturated ammonium chloride aq solution. Then, the organic layer was filtered off, and the solid residue was treated with 10% hydrochloric acid and extracted with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate and, after filtration, concentrated to give 121 g of a crude (1S)-2-(1-naphthyl)-1,7,7-trimethylbicyclo [2.2.1]-heptan-2-ol as an oil.

Workup

  1. temperaturethe whole was heated
  2. temperatureunder reflux for 72 hours
  3. customThe reaction was terminated
  4. temperatureby cooling with ice-water
  5. additionadding saturated ammonium chloride aq solution
  6. filtrationThen, the organic layer was filtered off
  7. additionthe solid residue was treated with 10% hydrochloric acid
  8. extractionextracted with diethyl ether
  9. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  10. filtrationafter filtration
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-3fbdc026031b4eec927943561ea0a7d6
Source dataset
uspto-grants-1994_11
Patent number
US05369109

Reaction notes

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