Hydrochloric Acid → 4-Tert-butyl-2-[5-(2-hydroxymethylphenylthiomethyl)benzofuran-2-yl]thiazole

HRID 487692Notes

Reaction equation

HRID 487692 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][S:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27](O)=[O:28])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][S:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][OH:28])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 190927324-Tert-butyl-2-[5-(2-carboxyphenylthiomethyl)benzofuran-2-yl]thiazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 190927354-Tert-butyl-2-[5-(2-hydroxymethylphenylthiomethyl)benzofuran-2-yl]thiazoleYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-tert-butyl-2-[5-(2-carboxyphenylthiomethyl)benzofuran-2-yl]thiazole (0.65 g) in tetrahydrofuran (10 ml), lithium aluminum hydride (0.12 g) was added under cooling with ice bath. After being stirred at ambient temperature for 5 hours, the resulting mixture was poured into a mixture of ice and diluted aqueous hydrochloric acid and extracted with toluene. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and toluene (1:9). The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-[5-(2-hydroxymethylphenylthiomethyl)benzofuran-2-yl]thiazole (0.45 g).

Workup

  1. additionwas added
  2. temperatureunder cooling with ice bath
  3. extractionextracted with toluene
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with a mixture of ethyl acetate and toluene (1:9)
  8. additionThe fractions containing object compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d6f3728273274dafbda171ab659c5b30
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

Loading…