Sulfuric Acid → 3-(2-Ethylbutyl)cyclobutanecarbaldehyde

HRID 1912092Notes

Reaction equation

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]

Participants

Conditions

Temperature: -78 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-73f7336ad9424a50a23573efe4aa2199
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604069B2

Reaction notes

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