Hydrochloric Acid → HCID 19603716, compound

HRID 1604641Notes

Reaction equation

HRID 1604641 reaction equation
[CH3:1][Mg]Br.[C:4]([C:8]1[N:9]=[C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][C:16]=3[CH:17]=2)[S:11][CH:12]=1)([CH3:7])([CH3:6])[CH3:5].Cl>O1CCCC1>[C:4]([C:8]1[N:9]=[C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([CH:22]([OH:23])[CH3:1])=[CH:18][C:16]=3[CH:17]=2)[S:11][CH:12]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 196038064-Tert-butyl-2-(5-formylbenzofuran-2-yl)thiazoleHCID 178418573HCID 178418573, compound

Product 1

HCID 19603716HCID 19603716, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl magnesium bromide (1M) in tetrahydrofuran (12.6 ml) was added dropwise over 30 minutes to a solution of 4-tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole (3.0 g) in tetrahydrofuran (30 ml) under ice-cooling. After being stirred at same temperature for 15 minutes, the reaction mixture was poured into ice-water. The mixture was neutralized with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate. The fractions containing the object compounds were combined and concentrated under recused pressure to give 4-tert-butyl-2-[5-(1-hydroxyethyl) benzofuran-2-yl]thiazole (2.04 g).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. washeluted with a mixture of n-hexane and ethyl acetate
  7. additionThe fractions containing the object compounds
  8. concentrationconcentrated under recused pressure

Sources & evidence

ORD record
ord-8fff2df5036b448ca5de0fa394b1d4da
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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