Water → 5-Methyloctahydro-1H-4,7-methanoinden-5-ol

HRID 2305976Notes

Reaction equation

HRID 2305976 reaction equation
[CH:1]12[CH2:11][CH:7]([C:8](=[O:10])[CH2:9]1)[CH:6]1[CH:2]2[CH2:3][CH2:4][CH2:5]1.[CH3:12][Mg]Cl.O>O1CCCC1>[CH3:12][C:8]1([OH:10])[CH2:9][CH:1]2[CH2:11][CH:7]1[CH:6]1[CH:2]2[CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962Water2×HCID 965094,7-Methano-5H-inden-5-one, octahydro-HCID 178418332HCID 178418332, compound

Product 1

HCID 134625055-Methyloctahydro-1H-4,7-methanoinden-5-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Tricyclo[5.2.1.02, 6]decan-8-one (15.0 g) in tetrahydrofuran (THF, 50 ml) is slowly added into CH3MgCl (9.7 g) in THF and the reaction mixture is stirred completely. Tetrahydrofuran (THF, 100 ml) with 5% of water is added into the reaction mixture. Then 100 ml of water is added to the reaction mixture. The reaction mixture is extracted by ether. The organic extract is concentrated in vacuo to yield 8-methyl-tricyclo[5.2.1.02,6]decan-8-ol (formula (X)) as white solid.

Workup

  1. extractionThe reaction mixture is extracted by ether
  2. extractionThe organic extract
  3. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-e2f8b642c84042a39b5a844ea98079b3
Source dataset
uspto-grants-2002_08
Patent number
US06441115B1

Reaction notes

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