(S)-3,7-dimethyloct-6-en-1-yl methanesulfonate → (R)-2,6-Dimethyl-oct-2-ene

HRID 130539Notes

Reaction equation

HRID 130539 reaction equation
[CH3:1][C@@H:2]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH2:3][CH2:4]OS(C)(=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:14][C:13](=[CH:12][CH2:11][CH2:10][C@H:2]([CH3:1])[CH2:3][CH3:4])[CH3:15]

Participants

4

Reactant 2

HCID 12016919(S)-3,7-dimethyloct-6-en-1-yl methanesulfonateHCID 21226445Aluminium lithium hydride3×

Product 1

HCID 11322496(R)-2,6-Dimethyl-oct-2-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To alkene 108 (60 g, 0.256 mol) in THF (1 L) at 0° C. was added lithium aluminum hydride (3.8 g, 0.128 mol). After 7 hours, a further 3.8 g of lithium aluminum hydride was added and the solution warmed to room temperature. After 18 hours, a further 3.8 g of lithium aluminum hydride was added. After a further 21 hours, the reaction was carefully quenched with 1N citric acid and the solution diluted further with brine. The resultant two phases were separated and the organic phase was dried (MgSO4) and concentrated to afford an oil which was used without further purification. MS, m/z (relative intensity): 139 [M−H, 100%].

Workup

  1. waitAfter 18 hours
  2. waitAfter a further 21 hours
  3. customthe reaction was carefully quenched with 1N citric acid
  4. additionthe solution diluted further with brine
  5. customThe resultant two phases were separated
  6. dry with materialthe organic phase was dried (MgSO4)
  7. concentrationconcentrated
  8. customto afford an oil which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-a347161107ef40d79086d5f86d9c4f49
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Reaction notes

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