Acetone → HCID 12892725、化合物

HRID 1879094ノート

反応式

HRID 1879094 の反応式
C[C:2]1(C)[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH2:4][C:3]1=[O:10].Cl.[CH3:13]C(C)=O>[Cl-].[Na+].O>[CH3:9][C:6]1([CH:8]=[CH2:13])[CH2:7][CH2:2][C:3](=[O:10])[CH2:4][CH2:5]1

参加物

5

反応物 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 583881972,2,4,4-Tetramethylcyclohexan-1-one

生成物 1

HCID 12892725HCID 12892725、化合物収率 94%

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

To a stirred solution of 2 (1.98 mmol, 360 mg) in acetone (7.76 mL) was added 10% aqueous hydrochloric acid solution (3.02 mL), and the resulting mixture was stirred at room temperature for 2.5 hours. The reaction mixture was then diluted with brine (40 mL) and extracted with methylene chloride/ethyl ether (1:2, 3×30 mL). The organic layers were combined and washed with saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (1×30 mL), then dried over magnesium sulfate, filtered, and concentrated in vacuo to give 19 (251.6 mg, 1.92 mmol, 94%) as a yellow oil that was used in the next reaction without further purification: 1H NMR (CDCl3) δ 5.89 (1H, dd, J=0.5, 17.3 Hz), 5.15 (1H, dd, J=1, 3.5 Hz), 5.12 (1H, dd, J=0.5, 10 Hz), 2.42-2.28 (4H, m), 1.97-1.91 (2H, m), 1.74-1.68 (2H, m), 1.12 (3H, s); 13C NMR (CDCl3) δ 212.4, 145.5, 112.9, 38.2, 37.1, 27.4; MS (EI) m/z 138.1 [M+], 123.1, 110.1, 105.1, 97.1, 86.0 (100%), 68.1, 63.0, 54.9; HRMS (EI) calcd for C9H14O 138.1045 found 138.1048.

後処理

  1. extractionextracted with methylene chloride/ethyl ether (1:2, 3×30 mL)
  2. washwashed with saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (1×30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4235b2156f0b480e8d76e36af82c290d
出典データセット
uspto-grants-2012_11
特許番号
US08314137B2

反応ノート

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