Cyclopropyl methyl ketone → 1-[4-Bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropylpropan-1,3-dione

HRID 863399ノート

反応式

HRID 863399 の反応式
[CH3:1][C:2]([CH:4]1[CH2:6][CH2:5]1)=[O:3].[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[C:10]([CH2:18][S:19][CH3:20])[CH:9]=1.[H-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](=[O:13])[CH2:1][C:2]([CH:4]2[CH2:6][CH2:5]2)=[O:3])=[C:10]([CH2:18][S:19][CH3:20])[CH:9]=1

参加物

6

反応物 4

HCID 13004Cyclopropyl methyl ketoneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 18978023Methyl 4-bromo-2-((methylthio)methyl)benzoate

生成物 1

HCID 189780111-[4-Bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropylpropan-1,3-dione収率 52.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of cyclopropyl methyl ketone (1.1 g) and methyl 4-bromo-2-(methylsulphenylmethyl)benzoate (3.6 g ) in tetrahydrofuran was added to a refluxing suspension of sodium hydride (80%, 0.9 g) in tetrahydrofuran. After the addition was complete, the mixture was maintained at reflux temperature for 30 minutes. It was then cooled and poured onto 100 g of ice and 50 ml of saturated aqueous sodium bicarbonate. The mixture was extracted with hexane, the organic solution dried (anhydrous sodium sulphate) and the solvent evaporated to give 1-[4-bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropylpropan-1,3-dione as an orange oil (2.23 g), NMR (CDCl3): 1.00(2H, m), 1.20(2H, m), 1.75(1H, m), 2.03(3H, s), 3.92(2H, s), 6.00(1H, s), 7.35(1H, m), 7.45(1H, m), 7.58(1H, m) 14.74(1H, s).

後処理

  1. additionAfter the addition
  2. temperaturethe mixture was maintained
  3. temperatureat reflux temperature for 30 minutes
  4. temperatureIt was then cooled
  5. extractionThe mixture was extracted with hexane
  6. dry with materialthe organic solution dried (anhydrous sodium sulphate)
  7. customthe solvent evaporated

出典と根拠

ORDレコード
ord-25995897a1334ab2873c2d6875997a50
出典データセット
uspto-grants-1998_02
特許番号
US05721193

反応ノート

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