Benzene → 5-(1-Hydroxypropyl)-3-phenylisoxazole

HRID 1742520

Reaction equation

HRID 1742520 reaction equation
C1(C(NCl)=[O:8])C=CC=CC=1.[CH:11]#[C:12][CH:13]([OH:16])[CH2:14][CH3:15].C([N:19]([CH2:22][CH3:23])CC)C.[CH:24]1C=[CH:28][CH:27]=[CH:26][CH:25]=1>>[OH:16][CH:13]([C:14]1[O:8][N:19]=[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:15]=1)[CH2:12][CH3:11]

Participants

5

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 929811-Pentyn-3-olHCID 12256294Benzamide, N-chloro-

Product 1

HCID 151807655-(1-Hydroxypropyl)-3-phenylisoxazole

Procedure

Dissolved in 200 ml of benzene were 18.5 g (0.12 mol) of benzenehydroxamic acid chloride synthesized in accordance with a known process [J.Org.Chem., 45, 3916 (1980)] and 10.0 g (0.12 mole) of 1-pentyne-3-ol, followed by the dropwise addition of 18 g (0.18 mol) of triethylamine under ice cooling. After they were reacted under reflux for 10 hours, the reaction mixture was washed with water and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (eluent: chloroform), whereby 5-(1-hydroxypropyl)-3-phenylisoxazole was obtained as colorless crystals. Analytical results of the crystals obtained: Yield: 19.3 g (79.7%). Melting point: 101°-102° C.

Workup

  1. customAfter they were reacted
  2. temperatureunder reflux for 10 hours
  3. washthe reaction mixture was washed with water
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by chromatography on a silica gel column (eluent: chloroform)

Sources & evidence

ORD record
ord-4618301d584947f1a421f6768e41ddc8
Source dataset
uspto-grants-1994_08
Patent number
US05338857

Linked notes

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