Cesium carbonate → HCID 86653261, compound
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[CH:2].Br[CH2:11][CH2:12][O:13][CH2:14][CH3:15].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O.CCOC(C)=O>[CH2:12]([O:13][CH2:14][CH2:15][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[CH:2])[CH:4]=1)[CH3:11]Participants
7
Conditions
- Temperature
- 90 °C
Procedure
3-Ethynylphenol (1.707 g, 12.45 mmol, 1.0 eq.) and 1-bromo-2-ethoxyethane (1.1 eq.) were taken up in DMF (20 mL), and Cs2CO3 (2.2 eq.) was added. The mixture was heated to 90° C. for 16 hours, and then cooled to room temperature. The mixture was diluted with water (50 mL) and EtOAc (30 mL), and the layers were separated. The organic layers were washed with water (2×50 mL) and brine (3×50 mL), and dried (MgSO4). The resulting residue was purified by chromatography (10% EtOAc/hexanes) to yield 1-(2-ethoxyethoxy)-3-ethynylbenzene as an oil (2.63 g, 96%).
Workup
- temperaturecooled to room temperature
- customthe layers were separated
- washThe organic layers were washed with water (2×50 mL) and brine (3×50 mL)
- dry with materialdried (MgSO4)
- customThe resulting residue was purified by chromatography (10% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-afa2a4a0e9ba48a892393901b3f90214
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338452B2
Reaction notes
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