Diethyl Ether → 2-(4-(Tert-butyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole

HRID 1185017Notes

Reaction equation

HRID 1185017 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([C:9]([NH:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCOCC>S(Cl)(Cl)=O>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([C:9]2[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 3200764-tert-Butyl-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide

Product 1

HCID 3200722-(4-(Tert-butyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazoleYield 57.1%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 101b (1000 g, crude) in thionyl chloride (1.5 L) was refluxed for 1 hour. The reaction mixture was cooled to room temperature and poured into 500 mL of stirred Et2O, during which time a white precipitate formed. The precipitate was collected by filtration and washed with Et2O, dissolved in 500 mL of water and neutralized with 25 percent NaOH. The yellow aqueous solution was extracted with EtOAC (3×500 mL) and the combined organic phase was washed with 500 mL of brine, dried over Na2SO4, filtered and concentrated in vacuo to provide 101c (530 g, 40.8% over 3 steps) as a white solid. 1HNMR (300 MHz, CDCl3) δ 7.87 (d, J=8.4 Hz, 2H), 7.41 (d, J=8.4 Hz, 2H), 4.08 (s, 2H), 1.37 (s, 6H), 1.33 (s, 9H).

Workup

  1. temperaturewas refluxed for 1 hour
  2. customformed
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with Et2O
  5. dissolutiondissolved in 500 mL of water and neutralized with 25 percent NaOH
  6. extractionThe yellow aqueous solution was extracted with EtOAC (3×500 mL)
  7. washthe combined organic phase was washed with 500 mL of brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb7c82a21a0f4704afeaf0db4c56efa1
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

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