Methanol → 5-(2-Benzyloxyethyl)-6-methyl-1,3-benzodioxole

HRID 2259755Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[C:19](Br)=[CH:18][C:14]2[O:15][CH2:16][O:17][C:13]=2[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([Li])CCC.CI.CO>CCOCC.CCCCCC.O>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[C:19]([CH3:21])=[CH:18][C:14]2[O:15][CH2:16][O:17][C:13]=2[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

3.0 g of 5-(2-benzyloxyethyl)-6-bromo-1,3-benzodioxole was dissolved in 100 ml of anhydrous ether. 8.5 ml of a 1.6 M solution of n-butyllithium in hexane was added to the solution at -78° C. and the reaction was conducted at -50° C. for 2 h. The reaction mixture was cooled again to -78° C. 6.4 g of methyl iodide was added thereto and the temperature was gradually elevated to room temperature. Methanol and water were added to the reaction mixture. After extraction with ethyl acetate, the extract was dried over magnesium sulfate and concentrated under reduced pressure to obtain a crude methyl compound. After purification according to silica gel column chromatography (ethylacetate/hexane=2:98), 1.9 g of the intended compound was obtained in the form of a pale yellow oil.

Workup

customwas gradually elevated to room temperature
extractionAfter extraction with ethyl acetate
dry with materialthe extract was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customto obtain a crude methyl compound
customAfter purification

Sources & evidence

ORD record: ord-560f79e7fb63408981b7ef9094600f7e
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05475024

Reaction notes

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