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

HRID 429010

Reaction equation

HRID 429010 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-b35a707df36243debca3a18a173342c1
Source dataset
uspto-grants-2001_11
Patent number
US06316159B1

Linked notes

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