Homoallyl bromide → 2-Cyclohexylhepta-1,6-dien-3-ol

HRID 634978Notes

Reaction equation

HRID 634978 reaction equation
[CH:1]1([C:7](=[CH2:10])[CH:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:11]([Mg]Br)=[CH:12][CH2:13][CH3:14].BrCCC=C.[Mg]>CCOCC>[CH:1]1([C:7]([CH:8]([OH:9])[CH2:14][CH2:13][CH:12]=[CH2:11])=[CH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 21241Homoallyl bromideHCID 5462224MagnesiumHCID 125770702-Cyclohexylprop-2-en-1-alHCID 178448305HCID 178448305, compound

Product 1

HCID 212616092-Cyclohexylhepta-1,6-dien-3-olYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

2-Cyclohexylprop-2-en-1-al (69 g, 0.5 mol) in 100 ml of ether was slowly added to but-1-enylmagnesium bromide prepared by slow addition of 4-bromo-but-1-ene (81.0 g, 0.6 mol) in 100 ml of ether at 0° C. to magnesium turnings (13.2 g, 0.55 mol) in 300 ml of ether. After the addition was complete, the reaction mixture was allowed to warm to room temperature (RT) and was stirred for additional 3 hours. After quenching with 2N HCl, the organic phase was separated, washed with H2O until neutral pH was achieved, dried (MgSO4), and the solvent was evaporated in vacuo. The crude product was distilled over a Vigreux column (0.15 Torr, 91° C.) yielding 85 g (88%) of pure product as colorless oil.

Workup

  1. additionAfter the addition
  2. customAfter quenching with 2N HCl
  3. customthe organic phase was separated
  4. washwashed with H2O until neutral pH
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated in vacuo
  7. distillationThe crude product was distilled over a Vigreux column (0.15 Torr, 91° C.)

Sources & evidence

ORD record
ord-fde7a86586644bed87f31b0b1e869e91
Source dataset
uspto-grants-2001_02
Patent number
US06184419B2

Reaction notes

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