Aluminium lithium hydride → (1-Formyl-2-naphthalen-2-ylethyl)carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([C:20](=[O:25])NCOC)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([CH:20]=[O:25])[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)([CH3:2])([CH3:4])[CH3:3]Participants
Conditions
- Temperature
- -55 °C
Procedure
To a solution of [1-(methoxymethylcarbamoyl)-2-naphthalen-2-ylethyl]carbamic acid tert-butyl ester, 67, (5.0 g, 13.4 mmol) in THF (40 mL) at −30° C. to −25° C. is added LAH (16.7 mL of a 1M solution in THF) over about 10 minutes and the reaction is then cooled to −55° C. and the stirring is continued for 3 hours. After cooling to −60° C., the reaction is quenched by the addition of citric acid in methanol (1:1 by weight). During quenching the temperature is maintained at about −45° C. The mixture is then allowed to warm to room temperature and partitioned between EtOAc and water and the water phase extracted again with EtOAc. The organic phases are combined and washed with sat NaCl, dried and concentrated in vacuo to afford the crude aldehyde as a white solid which is used without further purification.
Workup
- temperatureAfter cooling to −60° C.
- customthe reaction is quenched by the addition of citric acid in methanol (1:1 by weight)
- customDuring quenching the temperature
- temperatureis maintained at about −45° C
- temperatureto warm to room temperature
- custompartitioned between EtOAc and water
- extractionthe water phase extracted again with EtOAc
- washwashed with sat NaCl
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3bcc3ad5af944641a39f0ca173a215de
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087759B2
Reaction notes
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