2,5-dichloro-3-(trifluoromethyl)pyridine → Methyl 4-{[3-chloro-5-(trifluoromethyl)-2-pyridyl]oxy}-5,8-dimethyl-1,1-dioxo-1,2,3,4-tetrahydro-1lambda6-thiochromene-6-carboxylate

HRID 378814Notes

Reaction equation

HRID 378814 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]([CH3:16])=[C:8]2[C:3]=1[CH:4]([OH:19])[CH2:5][CH2:6][S:7]2(=[O:18])=[O:17].Cl[C:21]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][C:24]([Cl:31])=[CH:23][N:22]=1.CC(C)([O-])C.[K+]>O1CCCC1>[Cl:31][C:24]1[C:23]([O:19][CH:4]2[C:3]3[C:8](=[C:9]([CH3:16])[CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:2]=3[CH3:1])[S:7](=[O:17])(=[O:18])[CH2:6][CH2:5]2)=[N:22][CH:21]=[C:26]([C:27]([F:29])([F:28])[F:30])[CH:25]=1

Participants

5

Reactant 3

HCID 110421442,5-dichloro-3-(trifluoromethyl)pyridineHCID 23665647Potassium tert-butoxideHCID 70247427Methyl 5,8-dimethyl-4-hydroxy-1,1-dioxo-1,2,3,4-tetrahydro-1lambda6-thiochromene-6-carboxylate

Product 1

HCID 70205749Methyl 4-{[3-chloro-5-(trifluoromethyl)-2-pyridyl]oxy}-5,8-dimethyl-1,1-dioxo-1,2,3,4-tetrahydro-1lambda6-thiochromene-6-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.48 g (1.7 mmol) of methyl 5,8-dimethyl-4-hydroxy-1,1-dioxo-1,2,3,4-tetrahydro-1λ6-thiochromene-6-carboxylate and 0.4 g (1.9 mmol) of 2,5-dichloro-3-(trifluoromethyl)pyridine were dissolved in 20 ml of tetrahydrofuran and subsequently admixed with 0.21 g (1.9 mmol) of potassium tert-butoxide. The mixture was stirred for 3 h and subsequently concentrated using a rotary evaporator. The residue was taken up in 100 ml of ethyl acetate, washed with sat. NaCl solution (2×20 ml), dried over MgSO4 and concentrated using a rotary evaporator. The residue was purified by chromatography (silica gel, ethyl acetate: heptane=1:3).

Workup

  1. concentrationsubsequently concentrated
  2. customa rotary evaporator
  3. washwashed with sat. NaCl solution (2×20 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customa rotary evaporator
  7. customThe residue was purified by chromatography (silica gel, ethyl acetate: heptane=1:3)

Sources & evidence

ORD record
ord-7aa7206b551c4e5d88792b97b8e4e763
Source dataset
uspto-grants-2001_10
Patent number
US06297196B1

Reaction notes

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