tert-Butyl mercaptan → 2-[2-Fluoro-6-(1,1-dimethylethylthio)phenyl]-4,4-dimethyl-2-oxazoline

HRID 378050Notes

Reaction equation

HRID 378050 reaction equation
[CH3:1][C:2]([SH:5])([CH3:4])[CH3:3].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](F)[C:8]=1[C:14]1[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=1.[H-].[Na+]>C1COCC1>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:5][C:2]([CH3:4])([CH3:3])[CH3:1])[C:8]=1[C:14]1[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=1

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 10987554Oxazole, 2-(2,6-difluorophenyl)-4,5-dihydro-4,4-dimethyl-

Product 1

HCID 186300152-[2-Fluoro-6-(1,1-dimethylethylthio)phenyl]-4,4-dimethyl-2-oxazolineYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methyl-2-propanethiol (2.7 g, 30 mmol), the compound of example g (3.17 g, 15 mmol), and NaH (0.79 g, 33 mmol) in THF (100 mL) was stirred at RT for 1d, then at reflux for 1d. This was then quenched with sat aq NaHCO3 (50 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 1:4 EtOAc/hexanes to afford 3.5 g of 2-[2-fluoro-6-(1,1-dimethylethylthio)phenyl]-4,4-dimethyl-2-oxazoline as a yellow oil, an 83% yield.

Workup

  1. customThis was then quenched with sat aq NaHCO3 (50 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by HPLC with 1:4 EtOAc/hexanes

Sources & evidence

ORD record
ord-c1014414c52848b7831a3399f3fcf9ad
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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