Triethylamine → 2-(4-(Methylsulfonyl)phenyl)-2-oxoethyl 2-(4-fluorophenyl)acetate

HRID 275478

反応式

HRID 275478 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[O:22]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:20][C:21]([C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=2)=[O:22])=[O:10])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

生成物 1

HCID 189338812-(4-(Methylsulfonyl)phenyl)-2-oxoethyl 2-(4-fluorophenyl)acetate収率 68%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of 4.45 g (28.9 mmol) of 4-fluorophenylacetic acid in 3.26 g (31.8 mmol) of triethylamine and 275 mL of acetonitrile was added 8.9 g (28.9 mmol) of 2-bromo-4'-(methylsulfonyl)acetophenone (prepared in Step 3) at ambient temperature. The reaction mixture was stirred for 30 minutes, concentrated in vacuo, and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography with ethyl acetate/hexane (1:1) gave 6.87 g (68%) of 2-(4-fluorophenyl)-1-[2-[4-(methylsulfonyl) phenyl]-2-oxoethoxy]ethanone as a colorless solid: NMR (CDCl3) δ 3.08 (s, 3H), 3.79 (s, 2H), 5.35 (s, 2H), 7.06 (s, t, J=9 Hz, 2H), 7.32 (dd, J=6and 9 Hz, 2H), 8.06 (s, 4H).

後処理

  1. concentrationconcentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography with ethyl acetate/hexane (1:1)

出典と根拠

ORDレコード
ord-3377be980e814afb9b03c36ff6557afe
出典データセット
uspto-grants-1995_02
特許番号
US05393790

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