Pentane → 2-(2-tert-Butylphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

HRID 610867Notes

Reaction equation

HRID 610867 reaction equation
[Li][C:2]([CH3:5])([CH3:4])[CH3:3].CCCCC.F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[O:19][CH2:20][C:21]([CH3:24])([CH3:23])[N:22]=1>C1COCC1>[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[O:19][CH2:20][C:21]([CH3:24])([CH3:23])[N:22]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8003PentaneHCID 108887942-(2-fluorophenyl)-4,4-dimethyl-2-oxazolineHCID 178418306HCID 178418306, compound

Product 1

HCID 131847512-(2-tert-Butylphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazoleYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.7M solution of t-BuLi in pentane (161 mL, 274 mmol) was added dropwise to a solution of 2-(2-fluorophenyl)-4,4-dimethyl-2-oxazoline [cf. Meyers A. I. and Williams B. E., Tetrahedron Letters, 223-226(1978)] (48.0 g., 249 mmol) in THF (320 mL), maintaining the reaction temperature between -45 and -40° C. with a dry-ice/acetone cooling bath. The resulting reaction mixture was maintained at ≤-40° C. with a dry-ice/acetonitrile bath, and monitored to completion by GLC over 20 min. This mixture was poured onto ice and extracted three times with ether. These extracts were combined, dried (MgSO4), concentrated and distilled under vacuum to afford 56.87 g of 2-(2-tert-butylphenyl)-4,4-dimethyl-2-oxazoline, a 93% yield.

Workup

  1. temperaturemaintaining the reaction temperature between -45 and -40° C. with a dry-ice/acetone cooling bath
  2. customThe resulting reaction mixture
  3. temperaturewas maintained at ≤-40° C. with a dry-ice/acetonitrile bath
  4. additionThis mixture was poured onto ice
  5. extractionextracted three times with ether
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-0ef7846b0e8340989b36b23fb111a016
Source dataset
uspto-grants-1999_12
Patent number
US05998466

Reaction notes

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