5-Phenyladamantan-2-one → 2-Methyl-5-phenyladamantan-2-ol

HRID 1015503노트

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HRID 1015503 반응식
[CH3:1][Mg]I.[C:4]1([C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([C:13]4=[O:20])[CH2:11]2)[CH2:17]3)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CCOCC.C1COCC1>[CH3:1][C:13]1([OH:20])[CH:12]2[CH2:18][CH:16]3[CH2:17][C:10]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)([CH2:19][CH:14]1[CH2:15]3)[CH2:11]2

참가 물질

5

반응물 2

HCID 128135085-Phenyladamantan-2-oneHCID 178418373HCID 178418373, 화합물

생성물 1

HCID 120380532-Methyl-5-phenyladamantan-2-ol수율 97%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Freshly prepared methylmagnesium iodide in ether (1 M, 85 mL), was added through a canola to 5-phenyladamantan-2-one (9.6 g, 42.5 mmol) obtained in step II, in THF (85 mL) at 0° C. After stirring at 0° C. for 0.5 h, the reaction mixture was quenched by adding sat. aq. NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with diisopropylether. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure to obtain 2-methyl-5-phenyl-adamantan-2-ol (9.9 g) as an off-white solid in 97% yield. M.R: 98-100.4° C. m/z (M+23) 265; 1H NMR (CDCl3) 300 MHz δ 7.42-7.28 (m, 4H), 7.24-7.18 (m, 1H), 2.47-2.26 (m, 2H), 2.14-2.09 (m, 3H), 1.96-1.70 (m, 6H), 1.61-1.57 (m, 2H), 1.42 (s, 3H). 13C NMR (CDCl3) 75 MHz δ 150.0, 128.1 (2C), 125.7, 124.8 (2C), 73.3, 44.0 (2C), 40.5 (2C), 39.6 (2C), 35.9, 32.0, 27.6.

후처리

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

출처 및 근거

ORD 기록
ord-51dffe76d96148098611da0480e6fc01
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985759B2

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