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

HRID 1015503ノート

反応式

HRID 1015503 の反応式
[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

参加物

5

反応物 2

HCID 128135085-Phenyladamantan-2-oneHCID 178418373HCID 178418373、化合物

生成物 1

HCID 120380532-Methyl-5-phenyladamantan-2-ol収率 97%

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 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.

後処理

  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

出典と根拠

ORDレコード
ord-51dffe76d96148098611da0480e6fc01
出典データセット
uspto-grants-2011_07
特許番号
US07985759B2

反応ノート

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