Propargyl alcohol → 3-[3,5-Bis(trifluoromethyl)phenyl]prop-2-yn-1-ol

HRID 67923ノート

反応式

HRID 67923 の反応式
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5](I)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:16]([OH:19])[C:17]#[CH:18]>C(NCC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([C:18]#[C:17][CH2:16][OH:19])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

参加物

6

反応物 2

HCID 7859Propargyl alcoholHCID 6309701-Iodo-3,5-bis(trifluoromethyl)benzene

生成物 1

HCID 27361793-[3,5-Bis(trifluoromethyl)phenyl]prop-2-yn-1-ol

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8021Diethylamine溶媒

実験手順

To a stirred solution of 3,5-bistrifluoromethyliodobenzene (which may be prepared as described by S. D. Ross et al, J. Amer. Chem. Soc. (1953), 75, 4967-4969; 340.1 g) in anhydrous diethylamine (665 ml), cooled to 10° C. and under an inert atmosphere, there were added successively copper (I) iodide (1.81 g) and dichlorobis(triphenylphosphine)palladium (3.51 g). 2-Propyn-1-ol (57.8 g) was then added dropwise over 20 minutes and the reaction mixture was then maintained, with stirring, at 25° to 30° C. for 4 hours. The reaction mixture was then maintained overnight, with stirring, at ambient temperature. The solvent was removed by evaporation under reduced pressure (water-pump) and the crystalline residue was partitioned between diethyl ether (670 ml) and water (200 ml). The ether layer was separated, washed with water (2×200 ml), dried over anhydrous sodium sulphate and evaporated under reduced pressure (water-pump). The solid residue thus obtained was distilled to give 1-(3,5-bistrifluoromethylphenyl)-prop-1-yn-3-ol, in the form of a white crystalline solid (231.7 g), m.p. 58°-60° C., b.p. 87°-91° C./1 mm Hg.

後処理

  1. temperaturethe reaction mixture was then maintained
  2. temperatureThe reaction mixture was then maintained overnight
  3. stirringwith stirring, at ambient temperature
  4. customThe solvent was removed by evaporation under reduced pressure (water-pump)
  5. customthe crystalline residue was partitioned between diethyl ether (670 ml) and water (200 ml)
  6. customThe ether layer was separated
  7. washwashed with water (2×200 ml)
  8. dry with materialdried over anhydrous sodium sulphate
  9. customevaporated under reduced pressure (water-pump)
  10. customThe solid residue thus obtained
  11. distillationwas distilled

出典と根拠

ORDレコード
ord-fbf7479b2e2f4b2195617b9ba5d7977e
出典データセット
uspto-grants-1982_08
特許番号
US04347252

反応ノート

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