Sodium hydride → 1-Benzyloxy-2-methyl-4-[2-(cyclopropylmethoxy)ethyl]-benzene

HRID 1906669Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][C:12]=1[CH3:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:21]1([CH2:24]Br)[CH2:23][CH2:22]1>CS(C)=O>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][O:19][CH2:24][CH:21]2[CH2:23][CH2:22]2)=[CH:13][C:12]=1[CH3:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a flask charged with redistilled dimethylsulphoxide (100 ml) and sodium hydride (50% dispersion, 4.28 g), at 60°-65° C. was added 2-(4-benzyloxy-3-methylphenyl)ethanol (18.0 g) followed by the dropwise addition of cyclopropylmethyl bromide (12.04 g). The reaction mixture was stirred at about 75° C. for 48 hours, poured on to ice-water (1000 ml) and extracted with vigorous stirring into diethyl ether (1000 ml). The ether layer was dried (MgSO4) and evaporated under reduced pressure to afford an oily residue. This residue was chromatographed on preparative high pressure liquid chromatography using petroleum ether (40°-60°) and petroleum ether/diethyl ether (5:1) as eluants. The desired fractions were collected and evaporated under reduced pressure to give 1-benzyloxy-2-methyl-4-[2-(cyclopropylmethoxy)ethyl]-benzene (13.0 g) as an oil.

Workup

extractionextracted
stirringwith vigorous stirring into diethyl ether (1000 ml)
dry with materialThe ether layer was dried (MgSO4)
customevaporated under reduced pressure
customto afford an oily residue
customThis residue was chromatographed on preparative high pressure liquid chromatography
custompetroleum ether (40°-60°) and petroleum ether/diethyl ether (5:1)
customThe desired fractions were collected
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-7db2bfc9a70f48e5b6192b4a1dec7c3c
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04652563

Reaction notes

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