Sulfuric Acid → 3-(2-Ethylbutyl)cyclobutanecarbaldehyde

HRID 1912092ノート

反応式

HRID 1912092 の反応式
CON(C)[C:4]([CH:6]1[CH2:9][CH:8]([CH2:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH2:7]1)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)O>C(Cl)Cl>[CH2:14]([CH:11]([CH2:12][CH3:13])[CH2:10][CH:8]1[CH2:9][CH:6]([CH:4]=[O:5])[CH2:7]1)[CH3:15]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 86675050N-Methoxy-N-methyl-3-(2-ethylbutyl)cyclobutanecarboxamide

生成物 1

HCID 866750513-(2-Ethylbutyl)cyclobutanecarbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of N-methoxy-N-methyl-3-(2-ethylbutyl)cyclobutanecarboxamide (13.2 g) in methylene chloride (35 mL) was added dropwise diisobutylaluminum hydride (1.0 M in methylene chloride)(76.0 mL) at −78° C. After stirring at −78° C. for 2.5 hr, 1 M sulfuric acid was added dropwise to the mixture. The mixture was stirred at ice temperature for 20 min. The organic layer was removed, and the aqueous layer was extracted with methylene chloride (15 mL×2). The combined organic layer was washed with 0.5 N sulfuric acid (50 mL×2), water (50 mL) and brine, then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate comprising the title compound was used in the next step.

後処理

  1. stirringThe mixture was stirred at ice temperature for 20 min
  2. customThe organic layer was removed
  3. extractionthe aqueous layer was extracted with methylene chloride (15 mL×2)
  4. washThe combined organic layer was washed with 0.5 N sulfuric acid (50 mL×2), water (50 mL) and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe sodium sulfate was filtered off

出典と根拠

ORDレコード
ord-73f7336ad9424a50a23573efe4aa2199
出典データセット
uspto-grants-2013_12
特許番号
US08604069B2

反応ノート

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