Hydrochloric Acid → HCID 22009618, compound

HRID 322327Notes

Reaction equation

HRID 322327 reaction equation
CO.[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[N:9]=[C:10]([C:13](OCC)=[O:14])[S:11][CH:12]=1.[BH4-].[Na+].Cl>O1CCCC1.O>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[N:9]=[C:10]([CH2:13][OH:14])[S:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 22009789Ethyl 4-(2-thienyl)-2-thiazolecarboxylate

Product 1

HCID 22009618HCID 22009618, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Methanol (1.5 ml) in tetrahydrofuran (2 ml) was added dropwise to a stirred and refluxed mixture of ethyl 4-(2-thienyl)-2-thiazolecarboxylate (1.36 g), sodium borohydride (0.35 g) and tetrahydrofuran (15 ml). After refluxing for 1 h, the reaction mixture was poured into water, acidified with 1N HCl and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated to give 4-(2-thienyl)-2-thiazolylmethanol (0.92 g, 82%). Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 113-114° C.

Workup

  1. temperaturerefluxed
  2. temperatureAfter refluxing for 1 h
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0834b41c5b974c25afd5b64a5112e4a0
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

Loading…