Methanol → 3-Acetoxy-3-(4-chlorophenyl)-3-(3-pyridyl)-1-propene

HRID 1649544Notes

Reaction equation

HRID 1649544 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)([OH:11])[CH:9]=[CH2:10])=[CH:4][CH:3]=1.C(N([CH2:23][CH3:24])CC)C.C[OH:26]>CN(C)C1C=CN=CC=1.C(OC(=O)C)(=O)C>[C:23]([O:11][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH:9]=[CH2:10])(=[O:26])[CH3:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 127170981-(4-Chlorophenyl)-1-(3-pyridyl)-2-propen-1-ol

Product 1

HCID 127171053-Acetoxy-3-(4-chlorophenyl)-3-(3-pyridyl)-1-propeneYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 1-(4-chlorophenyl)-1-(3-pyridyl)-2-propen-1-ol (0.692 g, 2.8 mmol), triethylamine (3.3 ml) and 4-dimethylaminopyridine (85 g) was stirred in acetic anhydride (0.9 ml) at 25° C. for 20 h. Methanol (1 ml) was added and after 10 min the mixture was concentrated in vacuo. Ether (25 ml) was added and the ether phase was washed with saturated NaHCO3 solution (3×15 ml) and dried over MgSO4. Evaporation of the solvent gave 0.725 g (90%) of the title compound, which was used in the palladium catalyzed amination according to Example 16.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionEther (25 ml) was added
  3. washthe ether phase was washed with saturated NaHCO3 solution (3×15 ml)
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f3cfc1b4986f496f87277adceebd0a10
Source dataset
uspto-grants-1983_11
Patent number
US04418065

Reaction notes

Loading…