Hydrochloric Acid → HCID 14874130, compound
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C@@H:8]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:9][C:10](OC)=[O:11].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl>O1CCCC1>[F:7][C@@H:8]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:9][CH2:10][OH:11]Participants
Procedure
Under nitrogen atmosphere, 1 ml of dry tetrahydrofuran (THF) and 88 mg (2.3 mM) of lithium aluminum hydride were placed in a two-necked round-bottomed flask and cooled on an ice path. To the mixture, a solution of 400 mg (2.1 mM) of methyl (S)-3-fluorononanoate in 1 ml of dry THF was added dropwise. The ice bath was removed and the resultant mixture was stirred for 2 hours at room temperature. After the reaction, the reaction vessel (flask) was cooled on an ice bath. To the resultant reaction mixture, 0.5 ml of saturated sodium sulfate was added, followed by stirring for 30 minutes. To the resultant mixture, 4 ml of 3M-hydrochloric acid (HCl) was added, followed by extraction with Et2O. The organic layer was washed with 5 wt. %-sodium hydrogencarbonate aqueous solution and dried with anhydrous magnesium sulfate, followed by distilling-off of the solvent under reduced pressure to obtain 270 mg (1.66 mM) of (S)-3-fluorononanol.
Workup
- customThe ice bath was removed
- customAfter the reaction
- temperaturethe reaction vessel (flask) was cooled on an ice bath
- additionwas added
- stirringby stirring for 30 minutes
- extractionfollowed by extraction with Et2O
- washThe organic layer was washed with 5 wt. %-sodium hydrogencarbonate aqueous solution
- dry with materialdried with anhydrous magnesium sulfate
Sources & evidence
- ORD record
- ord-1fbfc6996d364b3bb2eeb39ce2fb923c
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05830386
Reaction notes
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