4-Methoxymethylene-1,1-dimethyl-cyclohexane → 4,4-Dimethylcyclohexane-1-carbaldehyde

HRID 1748164ノート

反応式

HRID 1748164 の反応式
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][C:7]([CH3:11])([CH3:10])[CH2:6][CH2:5]1>C1COCC1>[CH3:10][C:7]1([CH3:11])[CH2:8][CH2:9][CH:4]([CH:3]=[O:2])[CH2:5][CH2:6]1

参加物

3

反応物 1

HCID 589086674-Methoxymethylene-1,1-dimethyl-cyclohexane

生成物 1

HCID 222352954,4-Dimethylcyclohexane-1-carbaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of flask 4-(methoxymethylene)-1,1-dimethylcyclohexane (2.3 g, 14.9 mmol) in a 4:1 THF/2N HCl mixture (100 mL) was refluxed fo(1 hour. The volatile was removed in vacuo and the residue was cooled to 0°C. and neutralized with 1N NaOH and extracted with Et2O (3×60 mL). The organic layer was washed with water (50 mL), brine (60 mL) and dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography with hexane-DCM 10% linear gradient as eluant to give the title compound as clear oil. 1H NMR (400 MHz, CDCl3) δ 9.64 (d, J=1.6 Hz, 1H), 2.19-2.12 (m, 1H), 1.79-1.72 (m, 2H), 1.59-1.40 (m, 5H), 1.25-1.18 (m, 1H), 0.92 (s, 3H), 0.87 (s, 3H). No ionization by LCMS.

後処理

  1. custom1 hour
  2. customThe volatile was removed in vacuo
  3. extractionextracted with Et2O (3×60 mL)
  4. washThe organic layer was washed with water (50 mL), brine (60 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography with hexane-DCM 10% linear gradient as eluant

出典と根拠

ORDレコード
ord-105ee5a9710f45f5a6038f5754e1cf3f
出典データセット
uspto-grants-2015_10
特許番号
US09150568B2

反応ノート

読み込み中…