Diisopropyl Ether → 16-Aminohexadecan-1-ol
Reaction equation
C(OC(C)C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](OC)=[O:31].[OH-].[Na+]>O.O1CCCC1>[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31]Participants
7
Procedure
In a mixed solvent of 75 ml of isopropyl ether and 25 ml of tetrahydrofuran was suspended 1.0 g of lithium aluminum hydride and to the suspension was added with stirring at room temperature 2.45 g of crystalline methyl 16-aminohexadecanoate and the mixture was stirred overnight. To the reaction solution were added successively 1 ml of water, 1 ml of a 10% aqueous solution of sodium hydroxide and 3 ml of water and the insolubles thus precipitated out were filtered off. The insolubles were extracted with a mixed solvent of chloroform and methanol. Then, the extract was combined with the filtrate and the mixture was distilled to afford the title compound as a colorless crystal.
Workup
- additionto the suspension was added
- customthe insolubles thus precipitated out
- filtrationwere filtered off
- extractionThe insolubles were extracted with a mixed solvent of chloroform and methanol
- distillationthe mixture was distilled
Sources & evidence
- ORD record
- ord-5640207301ec449fa439c4eff4c6f059
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05972943
Reaction notes
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