Benzoyl chloride → HCID 19741704, compound

HRID 2255119Notes

Reaction equation

HRID 2255119 reaction equation
[C:1]([NH:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]=[CH2:18])=[C:12]([OH:19])[CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)(Cl)Cl.CCN(CC)CC>[C:1]([NH:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]=[CH2:18])=[C:12]([O:19][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:27])[CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 19741711HCID 19741711, compound

Product 1

HCID 19741704HCID 19741704, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

A solution of methyl α-(acetylamino)-3-hydroxy-4-(2-propenyl)benzeneacetate from Preparation 6 (1.5 g, 5.7 mmol) in CHCl3 (20 ml) and Et3N (1 ml) is treated with benzoyl chloride (1.0 g, 7.1 mmol). The resulting solution is stirred at room temperature for 4.5 hours. The reaction mixture is concentrated and the residue partitioned between EtOAc and saturated aqueous NaHCO3. The organic phases are combined, dried (MgSO4) and concentrated. The residue is purified by silica gel chromatography (50% EtOAc/Heptane). An oil of methyl α-(acetylamino)-3-[(phenylcarbonyl)oxy]-4-(2-propenyl)benzeneacetate is obtained (2.1 g, quantitative).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue partitioned between EtOAc and saturated aqueous NaHCO3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel chromatography (50% EtOAc/Heptane)

Sources & evidence

ORD record
ord-d0a64b372bb7431d845d8f07b1271934
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

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