Tetrahydrofuran → 2-Amino-1-(3-phenoxyphenyl)ethan-1-ol
Reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[C:12]([CH:14]([OH:17])[C:15]#[N:16])[CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[OH-].[Na+]>O>[NH2:16][CH2:15][CH:14]([C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([O:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:13]=1)[OH:17]Participants
Procedure
10 g of 3-phenoxybenzaldehyde cyanohydrin were added dropwise to a mixture of 5.1 g of lithium aluminum hydride and 500 ml of tetrahydrofuran, whilst ice-cooling, and the resulting mixture was heated under reflux for 4 hours. At the end of this time, 5 ml of water, 6 ml of a 15% w/v aqueous solution of sodium hydroxide and 18 ml of water were added in that order to the reaction mixture, whilst ice-cooling. Insoluble materials were filtered off, and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 3:1 by volume mixture of ethyl acetate and ethanol as the eluent, to give the title compound having an Rf=0.32 (thin layer chromatography over silica gel, using a 5:5:1 by volume mixture of ethyl acetate, ethanol and triethylamine as the developing solvent).
Workup
- temperaturecooling
- temperaturethe resulting mixture was heated
- temperatureunder reflux for 4 hours
- temperaturecooling
- filtrationInsoluble materials were filtered off
- concentrationthe filtrate was concentrated by evaporation under reduced pressure
- customThe concentrate was purified by column chromatography through silica gel
- additionby volume mixture of ethyl acetate and ethanol as the eluent
Sources & evidence
- ORD record
- ord-cc7dde0eedf24611a2f4723c8b1b7988
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576340
Reaction notes
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