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

HRID 368634Notes

Reaction equation

HRID 368634 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 1 d, then at reflux for 1 d. 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. temperatureat reflux for 1 d
  2. customThis was then quenched with sat aq NaHCO3 (50 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by HPLC with 1:4 EtOAc/hexanes

Sources & evidence

ORD record
ord-4613d2749c3b460ebefbb0bb103142c3
Source dataset
uspto-grants-2000_10
Patent number
US06133252

Reaction notes

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