Hydrochloric Acid → HCID 22221030, compound

HRID 1794331Notes

Reaction equation

HRID 1794331 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[CH:9][C:8]=2[C:12](OCC)=[O:13])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12][OH:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22220938HCID 22220938, compound

Product 1

HCID 22221030HCID 22221030, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(5-chloro-2-thienyl)isoxazole-4-carboxylate (9.00 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.5 M toluene solution, 52 ml) at 0° C. and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was poured into dilute hydrochloric acid, and the precipitated 5-(5-chloro-2-thienyl)-4-isoxazolylmethanol (7.00 g, yield 93%) was filtrated and recrystallized from ethyl acetate-hexane to give a colorless needle. melting point: 80–81° C.

Workup

  1. customat 0° C.

Sources & evidence

ORD record
ord-b627f30b182848d7abaaf1cf8e88caa1
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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