Sodium Hydroxide → HCID 131718277, compound

HRID 327306Notes

Reaction equation

HRID 327306 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]1[C@@H:13]2[C@@H:14]([CH3:17])[CH2:15][CH2:16][C@@H:12]2[C:11]([C:18](OC)=[O:19])=[CH:10][O:9]1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.CC(C)=O>[OH:19][CH2:18][C:11]1[C@H:12]2[CH2:16][CH2:15][C@H:14]([CH3:17])[C@H:13]2[C@H:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[O:9][CH:10]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21225700DiisobutylaluminumhydrideHCID 131718278HCID 131718278, compound

Product 1

HCID 131718277HCID 131718277, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl (1S, 4aS, 7S, 7aR)-1, 4a, 5, 6, 7, 7a-hexahydro-1-(2-tetrahydropyranyloxy)-7-methylcyclopenta[c]pyran-4-carboxylate (1.25 g, 0.0042 mol) obtained in Example 10 was dissolved in 20 ml of anhydrous tetrahydrofuran, and the reaction solution was cooled by ice in the atmosphere of an argon gas. Then, 7 ml of diisobutylaluminum hydride (1.5 mol, toluene solution) was added dropwise. After the reaction mixture was stirred at the same temperature for 2 hours, 1 ml of acetone was added and furthermore, a 3% aqueous sodium hydroxide solution was added dropwise. The reaction mixture solution was stirred for 1 hour. Magnesium sulfate was added to the solution and 20 minutes later, insoluble matters were filtered by a celite and concentrated under a reduced pressure. The resulting colorless oily substance, i.e., (1S, 4aS, 7S, 7aR)-1, 4a, 5, 6, 7, 7a-hexahydro-4-(hydroxymethyl)-1-(2-tetrahydropyranyloxy)-7-methylcyclopenta[c]pyran (0.95 mg, yield=83.9%) had the following physicochemical properties:

Workup

  1. temperaturethe reaction solution was cooled by ice in the atmosphere of an argon gas
  2. stirringThe reaction mixture solution was stirred for 1 hour
  3. filtrationinsoluble matters were filtered by a celite
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-fa31736b30b441698b7cd8d8e99d9877
Source dataset
uspto-grants-1993_12
Patent number
US05272172

Reaction notes

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