Tetrahydrofuran → HCID 15713905, compound

HRID 703638Notes

Reaction equation

HRID 703638 reaction equation
C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O[C:13]1([C:24]#[C:25][CH:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:18]([CH3:20])([CH3:19])[CH2:17][CH:16]([OH:21])[CH2:15][C:14]1([OH:23])[CH3:22].[OH-].[Na+]>O>[OH:23][C:14]1([CH3:22])[CH2:15][CH:16]([OH:21])[CH2:17][C:18]([CH3:19])([CH3:20])[C:13]1=[C:24]=[CH:25][CH:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22150762HCID 22150762, compound

Product 1

HCID 15713905HCID 15713905, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 10 ml of an anhydrous THF suspension containing 383 mg of lithium aluminum hydride was slowly added 10 ml of an anhydrous THF solution containing 1.0 g of 1-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)-oct-1-yn-3-ol over 10 minutes under ice-cooling in a nitrogen atmosphere. After the addition, the mixture was placed under refluxing conditions and stirred for 15 hours. After completion of the reaction, the reaction mixture was cooled, and 0.4 ml of water, 0.4 ml of a 15% sodium hydroxide aqueous solution, and 1.2 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 596 mg (yield: 63%) of 1-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)oct-1-en-3-ol.

Workup

  1. temperaturecooling in a nitrogen atmosphere
  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-e1092049491e4248a094aabf16c2fa83
Source dataset
uspto-grants-1991_01
Patent number
US04983723

Reaction notes

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