tert-Butyl acrylate → tert-Butyl 3-[2-(4-bromophenyl)ethoxy]propanoate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[CH:24]=[CH2:25]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:25][CH2:24][C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:4][CH:3]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
2-(4-Bromophenyl)ethanol (5 g) was treated with benzyltrimethylammonium hydroxide (Triton B®) (0.3 mL) and the resultant mixture was stirred in vacuo for 30 minutes. The mixture was then cooled to 0° C. and treated with t-butyl acrylate (3.5 g). The reaction was warmed to room temperature and stirred for 5 hours. The mixture was filtered through aluminium oxide (15 g) eluting with ether (75 mL). The collected filtrate was concentrated and purified by flash chromatography eluting with ethylacetate:iso-hexane (1:8) to give the sub-titled compound (5.42 g) as an oil.
Workup
- temperatureThe reaction was warmed to room temperature
- filtrationThe mixture was filtered through aluminium oxide (15 g)
- washeluting with ether (75 mL)
- concentrationThe collected filtrate was concentrated
- custompurified by flash chromatography
- washeluting with ethylacetate:iso-hexane (1:8)
Sources & evidence
- ORD record
- ord-439c951efb204572a5b85acff77ebe64
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709511B2
Reaction notes
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