Diethyl Ether → HCID 10537075, compound

HRID 623222Notes

Reaction equation

HRID 623222 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[CH2:8]([OH:12])[CH2:9][C:10]#C.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O:22]CC)C>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:6]2[CH:7]=[C:10]([CH2:9][CH2:8][OH:12])[O:22][N:3]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 7964ChlorobenzeneHCID 8471TriethylamineHCID 135663-Butyn-1-OL

Product 1

HCID 10537075HCID 10537075, compoundYield 55%

Procedure

5.05 g (5 mmol) of triethylamine in 20 ml of diethyl ether were added dropwise at -10° C. to a solution of 3.86 g (5.5 mmol) of 3-butyn-1-ol and 9.50 g (5 mmol) of 4-chlorobenzene N-hydroxycarboximidoyl chloride in 200 ml of dry diethyl ether. After 3 hours the reaction mixture was filtered, the filtrate was evaporated and the residue was recrystallized from ethyl acetate/hexane to yield 6.15 g (55%) of 3-(4-chlorophenyl)-5-isoxazolyl-2-ethanol of melting point 65.5°-67.5° C. after crystallization from ethyl acetate.

Workup

  1. filtrationAfter 3 hours the reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7d0623f50a9d45569bbc85c5ef8aec40
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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