Tetrahydrofuran → HCID 15713913, compound

HRID 703643Notes

Reaction equation

HRID 703643 reaction equation
C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:15][CH:16]([C:18]#[C:19][C:20]12[O:28][C:21]1([CH3:27])[CH2:22][CH2:23][C:24]2([CH3:26])[CH3:25])[CH3:17])(=O)C.[OH-].[Na+]>O>[OH:28][C:21]1([CH3:27])[CH2:22][CH2:23][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 22150763HCID 22150763, compound

Product 1

HCID 15713913HCID 15713913, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 20 ml of an anhydrous THF suspension containing 644 mg of lithium aluminum hydride was slowly added 20 ml of an anhydrous THF solution containing 2.0 g of 2-acetoxy-4-(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 10 hours. After completion of the reaction, the reaction mixture was cooled, and 0.6 ml of water, 0.6 ml of a 15% sodium hydroxide aqueous solution, and 1.8 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 1.2 g (yield: 70%) of 4-(2-hydroxy-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-6d5321469df44971bc784707c5bd8c19
Source dataset
uspto-grants-1991_01
Patent number
US04983723

Reaction notes

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