Dimethylformamide → HCID 89768162, compound

HRID 591410Notes

Reaction equation

HRID 591410 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.CN(C=O)C.Cl[CH2:16][C:17](=[O:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20]>O>[OH:9][C:4]1[CH:3]=[C:2]([S:1][CH2:16][C:17](=[O:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:7]=[C:6]([OH:8])[CH:5]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 36240Methyl 4-chloroacetoacetateHCID 20487371HCID 20487371, compound

Product 1

HCID 89768162HCID 89768162, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 5-sulfanylbenzene-1,3-diol (12.2 g) and DMF (dry) (100 mL) was added methyl 4-chloroacetoacetate (10.0 mL) at room temperature, and the mixture was stirred at 70° C. for 4 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with 1N HCl 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 (15.1 g).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with 1N HCl 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-d6eae492b00c4733988b3f803c53f378
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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