Pyridine → HCID 68003170, compound

HRID 1957920Notes

Reaction equation

HRID 1957920 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[C:10](\[CH3:13])/[CH2:11][OH:12])=[CH:5][CH:4]=1)[CH3:2].[C:14](OC(=O)C)(=[O:16])[CH3:15].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.ClCCl>[C:14]([O:12][CH2:11]/[C:10](/[CH3:13])=[CH:9]/[C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 67151063HCID 67151063, compound

Product 1

HCID 68003170HCID 68003170, compoundYield 1,790%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(E)-3-(4-Ethylphenyl)-2-methyl-2-propen-1-ol (4.6 g, 26 1 mmol, obtained by LiAlH4 reduction of (E)-3-(4-ethylphenyl)-2-methyl-2-propenal as described for (E)-2-Ethyl-3-(4-methylphenyl)-2-propen-1-ol) was added to a mixture of acetic anhydride (4.0 g, 39 mmol), pyridine (3.5 g, 44 mmol) and DMAP (0.46 g, 3.7 mmol) in 50 ml of dichloromethane. The mixture was stirred for 20 hours at room temperature. The dichloromethane was removed on a rotary evaporator, and the residue dissolved in EtOAc. This solution was washed with aqueous 10% HCl, aqueous 10% NaOH, and saturated aqueous NaCl. The organic phase was dried (MgSO4), filtered and concentrated. The product was purified by silica gel flash chromatography (hexane/EtOAc=80:20) followed by Kugelrohr distillation (140-160° C., 0.05 mbar) yielding 3.9 g (17.9 mmol, 69% yield) of the product as a colorless oil.

Workup

  1. customThe dichloromethane was removed on a rotary evaporator
  2. dissolutionthe residue dissolved in EtOAc
  3. washThis solution was washed with aqueous 10% HCl, aqueous 10% NaOH, and saturated aqueous NaCl
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by silica gel flash chromatography (hexane/EtOAc=80:20)
  8. distillationfollowed by Kugelrohr distillation (140-160° C., 0.05 mbar)

Sources & evidence

ORD record
ord-bf1269e6769f47e1abadfb3259e55bc8
Source dataset
uspto-grants-2013_04
Patent number
US08410042B2

Reaction notes

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