Water → 2-(Benzyloxy)-5-(dimethoxymethyl)benzyl alcohol
Reaction equation
[H-].[Al+3].[H-].[H-].[CH2:5]([O:12][C:13]1[CH:22]=[CH:21][C:20]([CH:23]([O:26][CH3:27])[O:24][CH3:25])=[CH:19][C:14]=1[C:15](OC)=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:5]([O:12][C:13]1[CH:22]=[CH:21][C:20]([CH:23]([O:24][CH3:25])[O:26][CH3:27])=[CH:19][C:14]=1[CH2:15][OH:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
Procedure
7 g of aluminum hydride was suspended in 200 ml tetrahydrofuran under ice-cooling, and a solution of 39.08 g of methyl 2-(benzyloxy)-5-(dimethoxymethyl)benzoate in 100 ml tetrahydrofuran was added thereto. After stirring for 5 minutes, water, 15% sodium hydroxide and water were added thereto and filtered. The filtrate was evapoarated, to give 35.15 g of 2-(benzyloxy)-5-(dimethoxymethyl)benzyl alcohol. This crude product was dissolved in 250 ml toluene, and 40 g of diphenyl phosphoryl azide and 22 ml diazabicylo[5.4.0]undecene were added, followed by stirring overnight at room temperature. Water was added to the reaction product, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was purified by silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (15:1), 17.4 g of 4-(benzyloxy)-3-(azidomethyl)dimethoxymethylbenzene was obtained. This product was left for 1 month at room temperature and purified by silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (12:1), 9.39 g of 4-(benzyloxy)-3-(azidomethyl)benzaldehyde was obtained.
Workup
- temperaturecooling
- filtrationfiltered
Sources & evidence
- ORD record
- ord-f6ddada85c8e40f380b78b1089927b18
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884821B1
Reaction notes
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