1,2-Dibromoethane → (3-[1,3]Dioxolan-2-yl-phenyl)-(5-methyl-thiophen-2-yl)-methanol

HRID 1927272Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.BrCCBr.[Mg].[CH3:18][C:19]1[S:23][C:22]([CH:24]=[O:25])=[CH:21][CH:20]=1>O.C1COCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:4]1[CH:3]=[C:2]([CH:24]([C:22]2[S:23][C:19]([CH3:18])=[CH:20][CH:21]=2)[OH:25])[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of THF (20 mL), 2-(3-bromophenyl)-1,3-dioxolane (2.7 g) and 1,2-dibromoethane (150 mg) was added magnesium (270 mg), which was heated to reflux for 10 minutes. The reaction mixture was cooled to 0° C., and a solution of 5-methyl-2-thiophencarbaldehyde (1.0 g) and THF (5 mL) was added thereto under stirring. The reaction solution was returned to room temperature and stirred for 10 minutes. Water was added to the reaction solution, which was then extracted with ethyl acetate. The solvent was evaporated from the organic layer under a reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1) to obtain the titled compound (1.1 g).

Workup

temperaturewas heated
temperatureto reflux for 10 minutes
customwas returned to room temperature
stirringstirred for 10 minutes
extractionwas then extracted with ethyl acetate
customThe solvent was evaporated from the organic layer under a reduced pressure
customthe residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-c2f170e5e12b45099e88c5aea51abef8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183264B2

Reaction notes

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