2,3-Dihydrofuran → Methyl 2-(Difluoromethyl)-4-(2-methylpropyl)-5-[(tetrahydro-2-furyl)thio]-6-(trifluoromethyl)-3-pyridinecarboxylate

HRID 1007243Notes

Reaction equation

HRID 1007243 reaction equation
[F:1][CH:2]([F:22])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([SH:17])=[C:5]([C:18]([F:21])([F:20])[F:19])[N:4]=1.[O:23]1[CH:27]=[CH:26][CH2:25][CH2:24]1>CCOCC.C1(C)C(S(O)(=O)=O)=CC=CC=1>[F:22][CH:2]([F:1])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([S:17][CH:24]2[CH2:25][CH2:26][CH2:27][O:23]2)=[C:5]([C:18]([F:21])([F:20])[F:19])[N:4]=1

Participants

5

Reactant 2

HCID 709342,3-DihydrofuranHCID 9974711Methyl 2-(difluoromethyl)-4-isobutyl-5-mercapto-6-(trifluoromethyl)-3-pyridinecarboxylate

Product 1

HCID 22668859Methyl 2-(Difluoromethyl)-4-(2-methylpropyl)-5-[(tetrahydro-2-furyl)thio]-6-(trifluoromethyl)-3-pyridinecarboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 69252-Methylbenzenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.07 g (0.021 mol) of compound 7, 2.92 g (0.042 mol) of dihydrofuran, and catalytic toluenesulfonic acid (9 mg) in 80 ml of ether was stirred overnight. The reaction mixture was concentrated in vacuo, and the residue was purified by HPLC (20% EtOAc in hexane) to give 5.82 g (68%) of the desired product as a yellow oil, n25D 1.5803.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by HPLC (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-167fcf480d8c4184af8fde52878fe624
Source dataset
uspto-grants-2004_09
Patent number
US06794396B2

Reaction notes

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