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

HRID 650297

Reaction equation

HRID 650297 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-ad544c725db040258fa7900dde80a2eb
Source dataset
uspto-grants-2001_08
Patent number
US06271412B1

Linked notes

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