Sodium Hydroxide → HCID 131718283, compound

HRID 1492672Notes

Reaction equation

HRID 1492672 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

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21225700DiisobutylaluminumhydrideHCID 131718284HCID 131718284, compound

Product 1

HCID 131718283HCID 131718283, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl (1S, 4aS, 7R, 7aR)-1-[1-(ethoxy)ethoxy]-1,4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[c]pyran-4carboxylate (3.00 g, 0.011 mol) obtained in Example 24 was dissolved in 70 ml of anhydrous tetrahydrofuran, and while the reaction mixture was being cooled with ice and stirred, 14.8 ml of diisobutylaluminum hydride (1.5M toluene solution) was added dropwise. The reaction mixture was stirred at the same temperature for 2 hours, 1.6 ml of acetone was added dropwise and the reaction mixture was again stirred for 20 minutes. Furthermore, 2 ml of 3% sodium hydroxide solution was added dropwise and the reaction mixture was stirred for 1 hour. After magnesium sulfate was added, the reaction mixture was further stirred for 20 minutes, unnecessary matters were filtered by a celite and the solvent was distilled off under a reduced pressure. A colorless oily substance was thus obtained, i.e., (1S, 4aS, 7R, 7aR)-1-[1-(ethoxy)ethoxy]-1,4a,5,6,7,7a-hexahydro-4-(hydroxymethyl)-7-methylcyclopenta[c]pyran (2.18 g, yield=81.5%). This (1S, 4aS, 7R, 7aR)-1-[1(ethoxy)ethoxy]-1,4a,5,6,7,7a-hexahydro-4-(hydroxymethyl)-7-methylcyclopenta[c]pyran had the following physicochemical properties:

Workup

  1. temperaturewhile the reaction mixture was being cooled with ice
  2. stirringThe reaction mixture was stirred at the same temperature for 2 hours
  3. stirringthe reaction mixture was again stirred for 20 minutes
  4. stirringthe reaction mixture was stirred for 1 hour
  5. stirringthe reaction mixture was further stirred for 20 minutes
  6. filtrationunnecessary matters were filtered by a celite
  7. distillationthe solvent was distilled off under a reduced pressure
  8. customA colorless oily substance was thus obtained

Sources & evidence

ORD record
ord-ac9fbc9b46ca46c799d0f13e238e7419
Source dataset
uspto-grants-1994_12
Patent number
US05374653

Reaction notes

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