HCID 12931926, compound → HCID 13719999, compound

HRID 926410Notes

Reaction equation

HRID 926410 reaction equation
[CH3:1][C:2]([OH:12])([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[C:3]#[C:4][CH3:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]([OH:12])([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])/[CH:3]=[CH:4]/[CH3:5]

Participants

4

Reactant 2

HCID 12931926HCID 12931926, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13719999HCID 13719999, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,8-dimethyl-7-nonen-2-yn-4-ol (7.78 g; 44.5 mmol) in dry THF (300 ml) was cooled into an ice-water bath, with stirring under nitrogen. Solid LiAlH4 (2.15 g; 53.8 mmol) was added all at once. After 5 minutes, the cooling bath is removed and the reaction is stirred for one hour, then refluxed for 4 hours. After cooling into an ice-water bath, the reaction was treated cautiously with water (2.2 mml), 5% aq. NaOH (6.6 ml) and water (2.2 ml). The reaction was warmed up to room temperature and stirred until a white slurry was observed. Solid anhydrous sodium sulfate (ca 20 g) was added to the mixture in order to dry the medium. The solid was filtered off, thoroughly rinsed with diethyl ether. The filtrate was concentrated in vacuo. The product was purified by column chromatography on silica gel (eluting with heptanes/ethyl acetate 3:1) followed by bulb-to-bulb distillation (75° C./1.2 mbar). The product was obtained as a liquid (3.8 g; 94% pure by GC; 21.3 mmol; yield: 48%).

Workup

  1. customthe cooling bath is removed
  2. stirringthe reaction is stirred for one hour
  3. temperaturerefluxed for 4 hours
  4. temperatureAfter cooling into an ice-water bath
  5. additionthe reaction was treated cautiously with water (2.2 mml), 5% aq. NaOH (6.6 ml) and water (2.2 ml)
  6. stirringstirred until a white slurry
  7. additionSolid anhydrous sodium sulfate (ca 20 g) was added to the mixture in order
  8. customto dry the medium
  9. filtrationThe solid was filtered off
  10. washthoroughly rinsed with diethyl ether
  11. concentrationThe filtrate was concentrated in vacuo
  12. customThe product was purified by column chromatography on silica gel (eluting with heptanes/ethyl acetate 3:1)
  13. distillationfollowed by bulb-to-bulb distillation (75° C./1.2 mbar)
  14. customThe product was obtained as a liquid (3.8 g; 94% pure by GC; 21.3 mmol; yield: 48%)

Sources & evidence

ORD record
ord-0f0b7b94831e49c385dc15fc5f211d2c
Source dataset
uspto-grants-2016_03
Patent number
US09284513B2

Reaction notes

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