Methyl trifluoroacetate → 2,2,2-Trifluoro-1-(4-vinylphenyl)ethanone

HRID 1007057ノート

反応式

HRID 1007057 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1)=[CH2:2].[F:11][C:12]([F:18])([F:17])[C:13](OC)=[O:14]>C1COCC1>[F:11][C:12]([F:18])([F:17])[C:13]([C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=1)=[O:14]

参加物

4

反応物 2

HCID 9893Methyl trifluoroacetateHCID 178436500HCID 178436500、化合物

生成物 1

HCID 225064842,2,2-Trifluoro-1-(4-vinylphenyl)ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The (4-vinylphenyl)magnesium bromide solution of Example 1 was cooled to −78° C. using a dry ice /acetone bath and a solution of methyl trifluoroacetate (20.00 g, 156.19 mmol) in THF (25 mL) was added dropwise over 15 min. The reaction mixture was stirred in the cooling bath for 1 h, then quenched by pouring into cold 1N H2SO4. The aqueous solution was extracted with ether and the combined extracts were washed with brine, dried (Na2SO4), and concentrated to provide 17.81 g of a pale yellow oil. This material was purified by vacuum distillation to provide 12.65 g (46%) of a colorless oil: bp 59-60° C. (1.4 mm); 1H NMR (CDCl3) δ 8.05 (d, 2ArH), 7.55 (d, 2ArH), 6.79 (dd, CH═), 5.97 (dd, ═CHH), 5.51 (dd ═CHH).

後処理

  1. customquenched
  2. additionby pouring into cold 1N H2SO4
  3. extractionThe aqueous solution was extracted with ether
  4. washthe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-ef1ea5b612c84277aee5f10c28418cd1
出典データセット
uspto-grants-2004_09
特許番号
US06794109B2

反応ノート

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