Dichloromethane → 2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl methoxy-ethanol
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[C:16](C4CO4)[CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH:23]1([CH2:26]O)[CH2:25][CH2:24]1.[C:28](=[O:31])([O-])[O-:29].[Na+].[Na+].Cl[CH2:35]Cl>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:26]([CH:23]4[CH2:24][CH2:25]4)[CH:28]([O:31][CH3:35])[OH:29])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1Participants
5
Procedure
To a solution of epoxide 30 (3.0 g, 0.0098 mol) in dichloromethane (30.0 ml) was added cyclopropyl methanol (60.0 ml) at ambient condition and stirred for 5 minutes. To the above solution was added boron trifluoride-ethyl ether complex (3.0 ml, 0.0238 mol) slowly at such a rate so as to maintain the temperature of reaction between 25° C. to 30° C. The reaction was stirred at ambient temperature for 18 hours. A saturated aqueous solution of sodium carbonate (3.0 g) was added carefully and the resulting mixture was extracted with dichloromethane (30 ml). The organic phase was separated followed by usual workup and FC to give ether-alcohol 44 (1.5 g, 40.5%).
Workup
- additionTo the above solution was added boron trifluoride-ethyl ether complex (3.0 ml, 0.0238 mol) slowly at such a rate so as
- temperatureto maintain
- customthe temperature of reaction between 25° C. to 30° C
- stirringThe reaction was stirred at ambient temperature for 18 hours
- extractionthe resulting mixture was extracted with dichloromethane (30 ml)
- customThe organic phase was separated
Sources & evidence
- ORD record
- ord-5a15d3ce1f644f92af85239b98d01a9a
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102665B2
Reaction notes
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