Cyclohexanone → 1-(3-Tert-butyl-phenyl)-4-methylene-cyclohexanol

HRID 132104

反応式

HRID 132104 の反応式
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].CCCCC.Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=1.[C:22]1(=[O:28])[CH2:27]CCC[CH2:23]1>O1CCCC1.[Cl-].[NH4+].C(OCC)(=O)C>[C:18]([C:14]1[CH:13]=[C:12]([C:22]2([OH:28])[CH2:27][CH2:3][C:1](=[CH2:4])[CH2:2][CH2:23]2)[CH:17]=[CH:16][CH:15]=1)([CH3:21])([CH3:20])[CH3:19]

参加物

8

反応物 4

HCID 7967CyclohexanoneHCID 8003PentaneHCID 3437981-Bromo-3-tert-butylbenzeneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 597337431-(3-Tert-butyl-phenyl)-4-methylene-cyclohexanol収率 81%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

実験手順

A solution of 1.7 M tert-butyllithium in pentane (32.0 mL, 54.4 mmol) was added to a solution of 1-bromo-3-tert-butyl-benzene (5.54 g, 26.0 mmol) in tetrahydrofuran (60 mL) at −78° C. After stirring for 1 h, cyclohexanone (2.00 g, 18.2 mmol) in tetrahydrofuran (15 mL) was added. After stirring for 18 h, during which time the solution warmed to ambient temperature, the solution was diluted with saturated aqueous ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 49:1, 24:1, 23:2 hexanes:ethyl acetate as the eluant to yield 3.61 g (81% yield) of 1-(3-tert-butyl-phenyl)-4-methylene-cyclohexanol as a yellow oil.

後処理

  1. stirringAfter stirring for 18 h, during which time the solution
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed with 49:1, 24:1, 23:2 hexanes

出典と根拠

ORDレコード
ord-f0668dfcdcd04782a255a587cf61429e
出典データセット
uspto-grants-2008_06
特許番号
US07385085B2

関連ノート

読み込み中…