Hydrochloric Acid → 2-(2-Thienyl)-5-benzoxazolylmethanol

HRID 322295Notes

Reaction equation

HRID 322295 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([C:15](OC)=[O:16])=[CH:11][C:9]=2[N:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>O1CCCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:9]=2[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22009751Methyl 2-(2-thienyl)-5-benzoxazolecarboxylate

Product 1

HCID 156622712-(2-Thienyl)-5-benzoxazolylmethanolYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(2-thienyl)-5-benzoxazolecarboxylate (1.50 g) in tetrahydrofuran (30 ml) was slowly added lithium aluminum hydride (220 mg) at 0° C., stirred for 30 minutes. To the reaction mixture was added water, which was made acidic with 1N-hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (4:1, v/v), 2-(2-thienyl)-5-benzoxazolyl methanol (1.03 g, 77%) was obtained. The recrystalization from ethyl acetate-hexane gave colorless needles, mp 158-159° C.

Workup

  1. customat 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-hexane (4:1

Sources & evidence

ORD record
ord-5671eaa417f9472e95066f05faaac23f
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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