5-Methoxyadamantan-2-one → 5-Methoxy-2-methyladamantan-2-ol

HRID 1015557

Reaction equation

HRID 1015557 reaction equation
[CH3:1][Mg]I.[CH3:4][O:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([C:9]3=[O:16])[CH2:7]1)[CH2:13]2>CCOCC.C1COCC1>[CH3:4][O:5][C:6]12[CH2:7][CH:8]3[CH2:14][CH:12]([CH2:11][CH:10]([C:9]3([CH3:1])[OH:16])[CH2:15]1)[CH2:13]2

Participants

5

Reactant 2

HCID 5283525-Methoxyadamantan-2-oneHCID 178418373HCID 178418373, compound

Product 1

HCID 120380545-Methoxy-2-methyladamantan-2-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Freshly prepared methyl magnesium iodide in ether (1M, 32 mL), was added through a canula to 5-methoxyadamantan-2-one (3.0 g, 16 mmol) in THF (32 mL) at 0° C. After stirring the mixture at 0° C. for 0.5 h, the reaction mixture was quenched by adding saturated aq. NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to obtain 5-methoxy-2-methyladamantan-2-ol as 1:1 anomeric mixture (3.0 g yield, 96%). m/z (M+23), 219; 1H NMR (CDCl3) 300 MHz δ 3.24 (s, 1½H), 3.23 ((s, 1½H), 2.68-2.62 (m, 1H), 2.40-1.55 (m, 10H), 1.53-1.35 (m, 2H), 1.38 (s, 3H).

Workup

  1. customthe reaction mixture was quenched
  2. additionby adding saturated aq. NH4Cl solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with diethyl ether
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-08dbba712f724b0e95edb0041678257b
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Linked notes

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