Potassium Carbonate → 4-Tert-butyl-2-(2-formyl-4-methoxyphenoxymethyl)thiazole

HRID 487671Notes

Reaction equation

HRID 487671 reaction equation
Br[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[N:7]=1.[OH:12][C:13]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:14]=1[CH:15]=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:8]([C:6]1[N:7]=[C:3]([CH2:2][O:12][C:13]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:14]=2[CH:15]=[O:16])[S:4][CH:5]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 196037502-Bromomethyl-4-tert-butylthiazole

Product 1

HCID 190928224-Tert-butyl-2-(2-formyl-4-methoxyphenoxymethyl)thiazoleYield 72.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromomethyl-4-tert-butylthiazole (3.4 g), 2-hydroxy-5-methoxybenzaldehyde (2.21 g) and potassium carbonate (2.0 g) in acetone (25 ml) was stirred under reflux for 7 hours. After being filtered, the filtrate was concentrated under reduced pressure to give a crude residue. The residue was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing object compound were combined and concentrated under reduced pressure to give a syrup. The syrup was crystallized from n-hexane and filtered to give 4-tert-butyl-2-(2-formyl-4-methoxyphenoxymethyl)thiazole (3.23 g).

Workup

  1. temperatureunder reflux for 7 hours
  2. filtrationAfter being filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a crude residue
  5. washeluted with a mixture of toluene and ethyl acetate
  6. additionThe fractions containing object compound
  7. concentrationconcentrated under reduced pressure
  8. customto give a syrup
  9. customThe syrup was crystallized from n-hexane
  10. filtrationfiltered

Sources & evidence

ORD record
ord-d52a2cf1a8b74187a4e11abb46edc4f6
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

Loading…