Tetrahydrofuran → HCID 15713909, compound

HRID 703644Notes

Reaction equation

HRID 703644 reaction equation
C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:15][CH:16]([C:18]#[C:19][C:20]12[O:32][C:21]1([CH3:31])[CH2:22][CH:23]([O:27]C(=O)C)[C:24]2([CH3:26])[CH3:25])[CH3:17])(=O)C.[OH-].[Na+]>O>[OH:32][C:21]1([CH3:31])[CH2:22][CH:23]([OH:27])[C:24]([CH3:25])([CH3:26])[C:20]1=[C:19]=[CH:18][CH:16]([OH:15])[CH3:17]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22150766HCID 22150766, compound

Product 1

HCID 15713909HCID 15713909, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 30 ml of an anhydrous THF suspension containing 808 mg of lithium aluminum hydride was slowly added 35 ml of an anhydrous THF solution containing 2.0 g of 2-acetoxy-4-(4-acetoxy-1,2-epoxy-2,5,5-trimethylcyclopentyl)but-3-yn under ice-cooling in a nitrogen atmosphere over 10 minutes. After the addition, the mixture was placed under refluxing conditions and stirred for 8 hours. After completion of the reaction, the reaction mixture was cooled, and 0.8 ml of water, 0.8 ml of a 15% sodium hydroxide aqueous solution, and 2.4 ml of water were carefully added thereto in this order, followed by vigorously stirring for 20 minutes. Any insoluble matter was removed by filtration with suction, and the filtrate was concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 902 mg (yield: 60%) of 4-(2,4-dihydroxy-2,5,5-trimethylcyclopentylidene)but-3-en-2-ol.

Workup

  1. temperaturecooling in a nitrogen atmosphere over 10 minutes
  2. additionAfter the addition
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled
  5. stirringby vigorously stirring for 20 minutes
  6. customAny insoluble matter was removed by filtration with suction
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting solid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a3499b91ed834cd39afa44d413a22cf8
Source dataset
uspto-grants-1991_01
Patent number
US04983723

Reaction notes

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