Propargyl alcohol → HCID 20294175, compound

HRID 1389951Notes

Reaction equation

HRID 1389951 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([CH2:14]O)[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.C(O)C#C.S(Cl)([Cl:24])=O>>[Cl:24][CH2:14][C:12]1[O:11][N:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:4]=2)[CH:13]=1

Participants

4

Reactant 3

HCID 7859Propargyl alcoholHCID 24386Thionyl Chloride2×HCID 64164586HCID 64164586, compound

Product 1

HCID 20294175HCID 20294175, compound

Procedure

To 17.6 g (0.0724 ml) of 3-(m-trifluoromethylphenyl-5-isoxazole methanol (prepared as described in Example 1 except that propargyl alcohol was used instead of propargyl bromide) was added 50 ml of thionyl chloride dropwise under nitrogen. After complete addition of thionyl chloride, the reaction mixture was heated on a steam bath for 30 minutes, thereafter excess thionyl chloride was removed under reduced pressure. The residue was triturated with hexane and an oil precipitate resulted. After partial removal of hexane in a rotary evaporator under reduced pressure, the oil precipitate crystallized and was filtered to give a tan solid, mp 33°-36° C. The tan solid (6 g) was recrystallized from hexane to give 3.0 g of brown solid, mp 33°-37° C. which was Kugelrohr distilled (1 mm, 140° C.) to give 2.9 g of solid, mp, 36°-38° C. Combined filtrates were concentrated and the residue (14.8 g) was Kugelrohr distilled (1 mm, 140° C.) to give 13.6 g of yellow oil which crystallized upon standing, mp 29°-36.5° C.; total yield 16.5 g (87%).

Workup

  1. temperaturethe reaction mixture was heated on a steam bath for 30 minutes
  2. customexcess thionyl chloride was removed under reduced pressure
  3. customThe residue was triturated with hexane
  4. customan oil precipitate resulted
  5. customAfter partial removal of hexane
  6. customin a rotary evaporator under reduced pressure
  7. customthe oil precipitate crystallized
  8. filtrationwas filtered
  9. customto give a tan solid, mp 33°-36° C
  10. customThe tan solid (6 g) was recrystallized from hexane

Sources & evidence

ORD record
ord-ec880e12ce184d17a79219419203efe3
Source dataset
uspto-grants-1981_01
Patent number
US04247322

Reaction notes

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