Sulfuric Acid → 3-Isobutylcyclobutanecarbaldehyde

HRID 1912045Notes

Reaction equation

HRID 1912045 reaction equation
CON(C)[C:4]([CH:6]1[CH2:9][CH:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:7]1)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)O>C(Cl)Cl>[CH2:10]([CH:8]1[CH2:9][CH:6]([CH:4]=[O:5])[CH2:7]1)[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 86675032N-Methoxy-N-methyl-3-isobutylcyclobutanecarboxamide

Product 1

HCID 840782283-Isobutylcyclobutanecarbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-methoxy-N-methyl-3-isobutylcyclobutanecarboxamide (77 g) in methylene chloride (235 mL) was added dropwise diisobutylaluminum hydride (1.0 M in methylene chloride) (473.2 mL) at −78° C. The mixture was stirred at −78° C. for 2 hr. After an addition of 1.5 M sulfuric acid (630 mL) at ice temperature, the mixture was extracted with methylene chloride. The combined organic layer was washed with 1.5 M sulfuric acid, water and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate comprising the title compound was used in the next step.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe combined organic layer was washed with 1.5 M sulfuric acid, water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off

Sources & evidence

ORD record
ord-7c23b604a7264a628e8aae9a3a0ba307
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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