Sulfuric acid magnesium salt (1:1) → 2-Cyclohexenone, 5,5-dimethyl-

HRID 418920

反応式

HRID 418920 の反応式
C[O:2][C:3]1[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5](=O)[CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].S([O-])([O-])(=O)=O.[Mg+2]>CCOCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH3:9][C:7]1([CH3:10])[CH2:8][C:3](=[O:2])[CH:4]=[CH:5][CH2:6]1

参加物

8

反応物 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 25517Ammonium ChlorideHCID 1383182-Cyclohexen-1-one, 3-methoxy-5,5-dimethyl-HCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 1383222-Cyclohexenone, 5,5-dimethyl-収率 58.6%

試薬・触媒・溶媒 3

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

Dissolve 3-methoxy-5,5-dimethyl-cyclohex-2-enone (Tetrahedron 57 (2001) 217-225) (10.6 g, 68.7 mmol) in ether (500 ml) cool to 0° C., add dropwise a 1.5M solution of diisobutyl aluminum hydride (68.7 ml, 103 mmol), and stir for 30 minutes. Add saturated aqueous ammonium chloride (25 ml), stir 1 hour, add anhydrous magnesium sulfate (10 g), stir 1 hour. Filter through celite and concentrate. Dissolve the residue in ether (500 ml), add toluene-4-sulfonic acid monohydrate (650 mg, 3.44 mmol) and water (6.2 ml), and stir 1 hour. Wash with saturated aqueous sodium bicarbonate, brine, dry and concentrate to give the title compound as a clear oil (5.0 g, 58%): 1H NMR (CDCl3) δ 6.89-6.84 (m, 1H), 2.28 (s, 2H), 2.26-2.24 (q, 2H), 1.06 (s, 6H).

後処理

  1. stirringstir 1 hour
  2. filtrationFilter through celite and
  3. concentrationconcentrate
  4. dissolutionDissolve the residue in ether (500 ml)
  5. stirringstir 1 hour
  6. washWash with saturated aqueous sodium bicarbonate, brine
  7. customdry
  8. concentrationconcentrate

出典と根拠

ORDレコード
ord-a57b2beb9e4b4899a89d3973c26d63cf
出典データセット
uspto-grants-2012_01
特許番号
US08093302B2

関連ノート

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