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

HRID 1015557

反応式

HRID 1015557 の反応式
[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

参加物

5

反応物 2

HCID 5283525-Methoxyadamantan-2-oneHCID 178418373HCID 178418373、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-08dbba712f724b0e95edb0041678257b
出典データセット
uspto-grants-2011_07
特許番号
US07985759B2

関連ノート

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