Dimethylformamide → HCID 89767847, compound

HRID 591498Notes

Reaction equation

HRID 591498 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:10])=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.CN(C=O)C.Cl[CH2:17][C:18](=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21].C([O-])([O-])=O.[K+].[K+]>O>[CH3:1][O:2][C:3]1[C:4]([CH3:10])=[C:5]([S:9][CH2:17][C:18](=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 36240Methyl 4-chloroacetoacetateHCID 19097670HCID 19097670, compound

Product 1

HCID 89767847HCID 89767847, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-methoxy-2-methylbenzenethiol (2.52 g) and DMF (dry) (10 mL) were added methyl 4-chloroacetoacetate (2.114 mL) and K2CO3 (2.60 g) at room temperature. The mixture was stirred at room temperature for 2 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (3.65 g).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-d7e1542defe3439299e461c443db3e29
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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