Diisobutylaluminumhydride → Methyl 3-butyl-1-formylcyclobutane-1-carboxylate

HRID 2055203ノート

反応式

HRID 2055203 の反応式
[CH3:1][O:2][C:3]([C:5]1([C:13](OC)=[O:14])[CH2:8][CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:6]1)=[O:4].[H-].C([Al+]CC(C)C)C(C)C>C(OCC)C>[CH3:1][O:2][C:3]([C:5]1([CH:13]=[O:14])[CH2:6][CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:8]1)=[O:4]

参加物

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 69222797Dimethyl 3-butylcyclobutane-1,1-dicarboxylate

生成物 1

HCID 71416977Methyl 3-butyl-1-formylcyclobutane-1-carboxylate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 3-butyl-cyclobutane-1,1-dicarboxylic acid dimethyl ester (8.37 g, 36.7 mmol) in diethyl ether (300 mL) at −78° C. under a nitrogen atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 49 mL, 73.4 mmol) dropwise. After 2.5 h, the reaction mixture was quenched with saturated aqueous NH4Cl solution (150 mL) then with 1N HCl solution (150 mL). The aqueous phase was extracted with diethyl ether (100 mL×5), was dried (MgSO4) and was evaporated in vacuo to yield the title compound as a clear, colorless oil (7.2 g, 100%) which was used without further purification. MH+199.

後処理

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl solution (150 mL)
  2. extractionThe aqueous phase was extracted with diethyl ether (100 mL×5)
  3. dry with materialwas dried (MgSO4)
  4. customwas evaporated in vacuo

出典と根拠

ORDレコード
ord-942e0f3865bf4dae91336ed209aaf127
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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