Tetrahydrofuran → HCID 15713908, compound

HRID 703636Notes

Reaction equation

HRID 703636 reaction equation
C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O[C:13]1([C:23]#[C:24][CH:25]([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][CH2:15][C:14]1([OH:22])[CH3:21].[OH-].[Na+]>O>[OH:22][C:14]1([CH3:21])[CH2:15][CH2:16][CH2:17][C:18]([CH3:19])([CH3:20])[C:13]1=[C:23]=[CH:24][CH:25]([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 14229047HCID 14229047, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15713908HCID 15713908, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 5 ml of an anhydrous THF suspension containing 274 mg of lithium aluminum hydride was slowly added 10 ml of an anhydrous THF solution containing 1.0 g of 1-(1,2-dihydroxy-2,6,6-trimethylcyclohexyl)oct-1-yn-3-ol under ice-cooling in a nitrogen atmosphere. 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 0.3 ml of water, 0.3 ml of a 15% sodium hydroxide aqueous solution, and 1.0 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 568 mg (yield: 60%) of 1-(2-hydroxy-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-8f0eb39100ad4a9d8b4e29b1363ea527
Source dataset
uspto-grants-1991_01
Patent number
US04983723

Reaction notes

Loading…