Sodium Hydroxide → HCID 131718274, compound
Reaction equation
[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[C@@H:12]2[C@@H:13]([CH3:16])[CH2:14][CH2:15][C@@H:11]2[C:10]([C:17](OC)=[O:18])=[CH:9][O:8]1)[CH3:5])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.CC(C)=O>[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[C@@H:12]2[C@@H:13]([CH3:16])[CH2:14][CH2:15][C@@H:11]2[C:10]([CH2:17][OH:18])=[CH:9][O:8]1)[CH3:5])[CH3:2]Participants
Conditions
- Temperature
- -50 °C
Procedure
Methyl (1S, 4aS, 7S, 7aR)-1-[1-(ethoxy)ethoxy]-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4carboxylate (15.0 g, 0.053 mol) obtained in Example 4 was dissolved in 250 ml of anhydrous tetrahydrofuran, and the reaction mixture was cooled to -50° C., 88 ml of diisobutylaluminum hydride (1.5 mol toluene solution) was added dropwise to this solution. After the reaction mixture was stirred at the same temperature for 3 hours, 10 ml of acetone was added and the solution was further stirred for 20 minutes. Furthermore, a 3% aqueous sodium hydroxide solution was added dropwise and the solution was stirred for 1 hour. After magnesium sulfate was added, the reaction solution was stirred further for 20 minutes, and after insoluble matters were removed by celite filtration, the solution was concentrated under a reduced pressure. The resulting colorless oily substance, i.e., (1S, 4aS, 7S, 7aR)-1-[1-(ethoxy)ethoxy]-1,4 a,5,6,7,7a-hexahydro-4-(hydroxymethyl)-7methylcyclopenta[c]pyran (12.1 g, yield=90.2%) had the following physicochemical properties:
Workup
- stirringthe solution was further stirred for 20 minutes
- stirringthe solution was stirred for 1 hour
- stirringthe reaction solution was stirred further for 20 minutes
- customafter insoluble matters were removed by celite filtration
- concentrationthe solution was concentrated under a reduced pressure
Sources & evidence
- ORD record
- ord-3b0244c624e54ee089b65dd66afa2654
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05374653
Reaction notes
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