4-Methyl-1-p-tolyl-pent-1-en-3-one → trans-4-Methyl-1-p-tolyl-1-penten-3-ol

HRID 915180Notes

Reaction equation

HRID 915180 reaction equation
[CH3:1][CH:2]([CH3:14])[C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1>CO>[CH3:1][CH:2]([CH3:14])[CH:3]([OH:13])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 3742474-Methyl-1-p-tolyl-pent-1-en-3-one

Product 1

HCID 69517116trans-4-Methyl-1-p-tolyl-1-penten-3-olYield 103.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methyl-1-p-tolyl-pent-1-en-3-one (77.0 g, 0.41 mol) in methanol (400 mL) was added slowly under argon sodium borohydride (31 g, 0.82 mol). The reaction was stirred at room temperature overnight and methanol (200 mL) was evaporated. The solution was neutralized with hydrochloric acid (2N), extracted with ethyl acetate. The organic layer was successively washed with water, aqueous NaHCO3, water and brine, dried (Mg2SO4), filtered and evaporated to give 80.4 g of trans-4-methyl-1(p-tolyl)-1-penten-3-ol and used without further purification in the next step (step h). 1H NMR (300 MHz; CDCl3): 0.94 (d, J=6.9 Hz, 3 H), 0.99 (d, J=6.6 Hz, 3 H), 1.83 (m, 1 H), 2.33 (s, 3 H), 4.01 (br, 1 H), 6.16 (dd, J1=7.0 Hz, J2=16.0 Hz, 1 H), 6.53 (d, J=16.0 Hz, 1 H), 7.12 (d, J=7.8 Hz, 1 H), 7.28 (d, J=7.8 Hz, 1 H).

Workup

  1. custommethanol (200 mL) was evaporated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with water, aqueous NaHCO3, water and brine
  4. dry with materialdried (Mg2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5430fc718b5c4f5283ad171eb55e4773
Source dataset
uspto-grants-2007_09
Patent number
US07265139B2

Reaction notes

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