HCID 86701847, compound → HCID 66747376, compound

HRID 1464895Notes

Reaction equation

HRID 1464895 reaction equation
[CH2:1]([C:5]1[CH2:10][CH2:9][C:8]([CH3:13])([CH:11]=[O:12])[CH2:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:14][Mg+].[Br-]>C(OCC)C>[CH2:1]([C:5]1[CH2:10][CH2:9][C:8]([CH:11]([OH:12])[CH3:14])([CH3:13])[CH2:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 86701847HCID 86701847, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 66747376HCID 66747376, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Isobutyl-1-methylcyclohex-3-enecarbaldehyde 3a (20 g, 111 mmol) was dissolved in diethyl ether (120 ml) and the solution stirred under nitrogen. An ice-bath was used to keep the temperature below 20° C. while MeMgBr (3M, 48 ml, 144 mmol) was added over 30 min. The ice-bath was removed and the reaction stirred for a further 30 min before being poured slowly, and under nitrogen, onto 2M HCl (50 ml). The phases were separated and the upper organic phase washed twice with brine (2×100 ml), dried (MgSO4) and concentrated in vacuo to give 19.6 g of a colorless oil. The product was purified by distillation (0.1 mbar, 90° C.) to give 4c as a 4:5 mixture of diastereomers containing 6.5% of a third isomer (14 g, 52% yield, colourless oil, 95% pure).

Workup

  1. customAn ice-bath was used
  2. customthe temperature below 20° C.
  3. additionwas added over 30 min
  4. customThe ice-bath was removed
  5. stirringthe reaction stirred for a further 30 min
  6. additionbefore being poured slowly
  7. customThe phases were separated
  8. washthe upper organic phase washed twice with brine (2×100 ml)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-495092a68138441caca4e1b3583c7c21
Source dataset
uspto-grants-2015_04
Patent number
US08999914B2

Reaction notes

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