Sodium Sulfate → HCID 57429404、化合物

HRID 2369772ノート

反応式

HRID 2369772 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][C:16](O)=[O:17])[CH2:9]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:9]1

参加物

5

反応物 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2 回HCID 574294053-(3-Methylcyclohexyl)propanoic acid

生成物 1

HCID 57429404HCID 57429404、化合物収率 64%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

LiAlH4 (16 g, 0.42 mol, 1.2 eq) and diethyl ether (450 mL) were charged into a 2 L three-necked round-bottom flask equipped with a mechanical stirrer and a reflux condenser and cooled at 0° C. The crude 3-(3-methylcyclohexyl)propanoic acid (60 g, 0.35 mol) was dissolved in diethyl ether (400 mL) and added dropwise to the reaction flask. The reaction mixture was then stirred for 3 h at ambient temperature. The excess of lithium aluminium hydride was hydrolyzed with saturated aqueous sodium sulphate and the mixture filtered. THF (1 L) was added to the residue and the suspension was heated to 35° C. for 1 h. The suspension was filtered and the combined organic layers were dried over sodium sulphate and evaporated to yield the crude product as an oil. Chromatography on a silica gel column with 8% EtOAc in hexane as elution agent, followed by a bulb-to-bulb distillation (0.1 mBar, 140° C.) gave pure 3-(3-methylcyclohexyl)propan-1-ol (35 g, gc purity>98%; yield=61%).

後処理

  1. customequipped with a mechanical stirrer and a reflux condenser
  2. additionadded dropwise to the reaction flask
  3. filtrationthe mixture filtered
  4. additionTHF (1 L) was added to the residue
  5. temperaturethe suspension was heated to 35° C. for 1 h
  6. filtrationThe suspension was filtered
  7. dry with materialthe combined organic layers were dried over sodium sulphate
  8. customevaporated
  9. customto yield the crude product as an oil
  10. washChromatography on a silica gel column with 8% EtOAc in hexane as elution agent
  11. distillationfollowed by a bulb-to-bulb distillation (0.1 mBar, 140° C.)

出典と根拠

ORDレコード
ord-d3a0fae7648f4f2b968bbcd0eb9bed62
出典データセット
uspto-grants-2014_04
特許番号
US08709994B2

反応ノート

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