Diethylamine → HCID 86757416, compound

HRID 1596723Notes

Reaction equation

HRID 1596723 reaction equation
Cl[C:2](/[CH:4]=[C:5](/[C:7]1[CH:8]=[CH:9][C:10]([O:17][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])\[CH3:6])=[O:3].[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>C1COCC1>[CH2:26]([N:28]([CH2:29][CH3:30])[C:2](/[CH:4]=[C:5](/[C:7]1[CH:8]=[CH:9][C:10]([O:17][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])\[CH3:6])=[O:3])[CH3:27]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86757417HCID 86757417, compound

Product 1

HCID 86757416HCID 86757416, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (E)-5-(2-chlorocarbonyl-1-methylvinyl)-2-(1-phenylethoxy)-benzoate (1.0 g, 2.79 mmol)in THF (50 mL) is added diethylamine (1.16 mL, 11.8 mmol), and the mixture is stirred at room temperature for 3 hours, after which time THF is removed in vacuo, and the residue is lssoved in CH2Cl2 (75 mL) and then washed with 1 N HCl (2×100 mL) and brine (1×50 mL), and dried over MgSO4. Chromatography (silica, 2:1 hexane/EtOAc) yields methyl (E)-5-(2-diethylcarbamoyl-1-methylvinyl)-2-(1-phenylethoxy)-benzoate.

Workup

  1. customafter which time THF is removed in vacuo
  2. washwashed with 1 N HCl (2×100 mL) and brine (1×50 mL)
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-49e8811098a44caeaa3d251ca6c68900
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

Loading…