Ammonium Chloride → 2-Methyl-2-adamantanol

HRID 623325

反応式

HRID 623325 の反応式
[CH2:1]1[CH:6]2[CH2:7][CH:8]3[C:10](=[O:11])[CH:4]([CH2:5]2)[CH2:3][CH:2]1[CH2:9]3.[CH3:12][Li].[NH4+].[Cl-]>CCOCC>[CH3:12][C:10]1([OH:11])[CH:4]2[CH2:5][CH:6]3[CH2:1][CH:2]([CH2:3]2)[CH2:9][CH:8]1[CH2:7]3

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 64151AdamantanoneHCID 178418348HCID 178418348、化合物

生成物 1

HCID 1365452-Methyl-2-adamantanol収率 95%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-adamantone (1.50 g, 10 mmol) in ether was added CH3Li (7.5 ml, 1.6M in ether, 12 mmol) dropwise at 0° C. under a N2 atmosphere. The mixture was stirred for another hr at 0° C., then brought to ambient temperature and stirred overnight. Saturated NH4Cl solution was added and extracted with ether for three times. The combined ether was dried over MgSO4 and concentrated in vacuo. The crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2) to give 56 as white solid (1.58 g, 95%). 1H-NMR (360 MHz, CDCl3) δ 2.20-2.16 (m, 2H), 1.89-1.75 (m, 6H), 1.68 (br s, 4H), 1.57-1.54 (m, 2H), 1.48 (br s, 1H), 1.35 (s, 3H); 13C-NMR (90 MHz, CDCl3) δ 74.06, 39.30, 38.49, 35.33, 33.16, 27.73, 27.60, 27.22; ESI-MS: Calculated for C11H18O (M+H)+ 167.3. Found: 167.3.

後処理

  1. custombrought to ambient temperature
  2. stirringstirred overnight
  3. extractionextracted with ether for three times
  4. dry with materialThe combined ether was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2)

出典と根拠

ORDレコード
ord-f7715c6b42eb4e2cb15b5435ca246d2a
出典データセット
uspto-grants-2016_04
特許番号
US09301950B2

関連ノート

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