Acetone → HCID 58502815、化合物

HRID 40471ノート

反応式

HRID 40471 の反応式
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)O)[CH:11]=2)=[CH:4][CH:3]=1.CC(C)=[O:25]>O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]3[C:16](=[O:15])[CH:17]=[CH:18][CH:14]3[OH:25])[CH:11]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 180AcetoneHCID 58502794(4'-Chloro-4-ethylbiphen-3-yl)furan-2-ylmethanol

生成物 1

HCID 58502815HCID 58502815、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

A solution of (4′-chloro-4-ethylbiphen-3-yl)furan-2-ylmethanol (67.18 g, 214.8 mmol) in acetone (1340 ml) and water (235 ml) is heated to 55° C. and 30 drops of polyphosphoric acid are added. The mixture is stirred at 55° C. for 25 hours, then cooled to room temperature. The reaction mixture is concentrated under reduced pressure to remove most of the acetone then ethyl acetate (600 ml) is added, and the reaction mixture is partitioned. The aqueous phase is extracted into ethyl acetate and the organic solutions are combined, washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 5-(4′-chloro-4-ethylbiphen-3-yl)-4-hydroxy-cyclopent-2-enone (59.84 g) as a brown oil.

後処理

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customto remove most of the acetone
  4. additionethyl acetate (600 ml) is added
  5. customthe reaction mixture is partitioned
  6. extractionThe aqueous phase is extracted into ethyl acetate
  7. washwashed with saturated aqueous sodium bicarbonate solution and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. customThe residue is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-19d4855be5024ea9a0f79a20a730ded4
出典データセット
uspto-grants-2013_09
特許番号
US08530388B2

反応ノート

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