Chloromethyl Methyl Ether → 4,5-(Dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenenitrile

HRID 1741952Notes

Reaction equation

C(N(C(C)C)CC)(C)C.[CH3:10][C:11]1([CH3:23])[O:22][CH:19]([CH:20]=[CH2:21])[CH:13]([CH:14]([OH:18])[CH2:15][C:16]#[N:17])[O:12]1.[CH3:24][O:25][CH2:26]Cl>C(OCC)C>[CH3:10][C:11]1([CH3:23])[O:22][CH:19]([CH:20]=[CH2:21])[CH:13]([CH:14]([O:18][CH2:24][O:25][CH3:26])[CH2:15][C:16]#[N:17])[O:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

Nine milliliters of diisopropylethylamine were added to 2.11 g of 4,5-(dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrile, and 2 ml of methoxymethyl chloride was then added to the mixture gradually at 0° C. After stir-ring at 0° C. for 16 hours, the reaction mixture was diluted with 300 ml of diethyl ether, and washed with 1N hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution in sequence. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was filtered by a silica gel column to afford 2.28 g of 4,5-(dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenenitrile having the following properties (yield 88 %).

Workup

additionwas then added to the mixture gradually at 0° C
washwashed with 1N hydrochloric acid
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
filtrationThe obtained residue was filtered by a silica gel column

Sources & evidence

ORD record: ord-cc1e16ef6d004cf8b60f5a7006aeb30b
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334740

Reaction notes

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