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

HRID 1015557

반응식

HRID 1015557 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-08dbba712f724b0e95edb0041678257b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985759B2

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