Diisobutylaluminumhydride → Methyl 1-formyl-4,4-dimethylcyclohexane-1-carboxylate

HRID 2055181ノート

反応式

HRID 2055181 の反応式
[CH3:1][C:2]1([CH3:16])[CH2:7][CH2:6][C:5]([C:12](OC)=[O:13])([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[H-].C([Al+]CC(C)C)C(C)C>C(OCC)C>[CH3:11][O:10][C:8]([C:5]1([CH:12]=[O:13])[CH2:6][CH2:7][C:2]([CH3:16])([CH3:1])[CH2:3][CH2:4]1)=[O:9]

参加物

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 45098019Dimethyl 4,4-dimethylcyclohexane-1,1-dicarboxylate

生成物 1

HCID 71416982Methyl 1-formyl-4,4-dimethylcyclohexane-1-carboxylate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of dimethyl 4,4-dimethyl-cyclohexane-1,1-dicarboxylate (5.23 g, 22.9 mmol) in diethyl ether (250 mL) at −78° C. under a nitrogen atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 30.6 mL, 45.9 mmol) dropwise. After 2.5 h, the reaction mixture was quenched with a mixture of methanol (75 mL) and water (75 mL). The mixture was filtered through Celite@ and the aqueous phase was extracted with diethyl ether (100 mL×5), was dried (MgSO4) and was evaporated in vacuo to yield the title compound which was used without further purification. MH+199.

後処理

  1. customthe reaction mixture was quenched with a mixture of methanol (75 mL) and water (75 mL)
  2. filtrationThe mixture was filtered through Celite@
  3. extractionthe aqueous phase was extracted with diethyl ether (100 mL×5)
  4. dry with materialwas dried (MgSO4)
  5. customwas evaporated in vacuo

出典と根拠

ORDレコード
ord-d14ccf4292bc4635b289ced3704b87ae
出典データセット
uspto-grants-2008_02
特許番号
US07332485B2

反応ノート

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