Triethylamine → 1-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethane

HRID 6977

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:18][S:19]([O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:3][CH:4]=1)(=[O:21])=[O:20]

Participants

Conditions

Temperature: -20 °C

Procedure

2-(4-Hydroxyphenyl)ethanol(356 g, 2.58 mol, 1.0 eq) was dissolved in methylene chloride (3500 ml) and triethyl amine (653 g, 6.44 mol, 2.5 eq). The mixture was cooled to −20° C. Methanesulfonyl chloride (657 g, 5.74 mol. 2.2 eq) was then added keeping the temperature between −25° C. and −15° C. When the conversion was >95% salts were formed which were filtered off and washed with methylene chloride (600 ml). The organic layer was washed first with saturated sodium hydrogencarbonate solution (700 ml) at 20° C. followed by water (700 ml). The methylene chloride was evaporated to dryness and the remaining residue was then used in the subsequent step.

Workup

customthe temperature between −25° C. and −15° C
customwere formed which
filtrationwere filtered off
washwashed with methylene chloride (600 ml)
washThe organic layer was washed first with saturated sodium hydrogencarbonate solution (700 ml) at 20° C.
customThe methylene chloride was evaporated to dryness

Sources & evidence

ORD record: ord-cdfc09446c49400d80ac411e2e633a6a
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084177B2

Linked notes

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