Sulfuric Acid → 4,5-(Dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenal

HRID 1741953Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[O:16][CH:13]([CH:14]=[CH2:15])[CH:4]([CH:5]([O:9][CH2:10][O:11][CH3:12])[CH2:6][C:7]#N)[O:3]1.[H-].C([Al+]C(C)C)(C)C.S(=O)(=O)(O)[OH:27]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:1][C:2]1([CH3:17])[O:16][CH:13]([CH:14]=[CH2:15])[CH:4]([CH:5]([O:9][CH2:10][O:11][CH3:12])[CH2:6][CH:7]=[O:27])[O:3]1

Participants

Conditions

Temperature: -40 °C

Procedure

4,5-(Dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenenitrile (159.8 mg) was dissolved in dry toluene, and 1.6 ml of 0.5N diisopropyl aluminum hydride was added at -78° C. The reaction mixture was stirred at -78° C. for 2 hours and at -40° C. for 30 minutes, and 5% dilute sulfuric acid was gradually added at 0° C. The reaction mixture was diluted with diethyl ether, and the organic layer was washed with a sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure to afford 91.1 mg of 4,5-(dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenal.

Workup

washthe organic layer was washed with a sodium chloride aqueous solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-98edb730e60d48819774689c181c6cdb
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334740

Reaction notes

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