Hexane ethyl acetate hexane → 3-Bromo-1,5-dimethyl-4-isopropoxy-8-oxa-bicyclo[3.2.1]octa-3,6-dien-2-one

HRID 502915ノート

反応式

HRID 502915 の反応式
[Br:1][C:2]1[C:3](=[O:13])[C:4]2([CH3:12])[O:10][C:7]([CH3:11])([C:8]=1Br)[CH:6]=[CH:5]2.[CH:14]([O-:17])([CH3:16])[CH3:15].[Li+].CCCCCC.C(OCC)(=O)C.CCCCCC.P([O-])(O)(O)=O.[Na+]>O1CCCC1.O>[Br:1][C:2]1[C:3](=[O:13])[C:4]2([CH3:12])[O:10][C:7]([CH3:11])([C:8]=1[O:17][CH:14]([CH3:16])[CH3:15])[CH:6]=[CH:5]2

参加物

7

反応物 4

HCID 21939919Hexane ethyl acetate hexaneHCID 23672064Monosodium phosphateHCID 23673350Lithium propan-2-olateHCID 684621593,4-Dibromo-1,5-dimethyl-8-oxa-bicyclo[3.2.1]octa-3,6-dien-2-one

生成物 1

HCID 586095313-Bromo-1,5-dimethyl-4-isopropoxy-8-oxa-bicyclo[3.2.1]octa-3,6-dien-2-one収率 68%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 2.74 g (8.9 mmol) of 3,4-dibromo-1,5-dimethyl-8-oxa-bicyclo[3.2.1]octa-3,6-dien-2-one (prepared according to Organic Lett. 4(12), 1997 (2002)) dissolved in 10 ml of tetrahydrofuran is added dropwise at ambient temperature to a solution of 5.4 ml (10.7 mmol) of 2M lithium isopropanolate diluted with 10 ml of tetrahydrofuran. The mixture is stirred for 3 hours at ambient temperature until the starting material has reacted completely (TLC monitoring: hexane/ethyl acetate/hexane 4:1). The reaction solution is then treated at a temperature of 0° C. with a 10% sodium dihydrogen phosphate solution (20 ml) and water (30 ml) and extracted three times with ethyl acetate. Drying over sodium sulfate and concentration by evaporation are carried out. For further purification, the dark oil so obtained is purified by chromatography over silica gel with 5% ethyl acetate in hexane. 1.73 g (68% of theory) of pure 3-bromo-1,5-dimethyl-4-isopropoxy-8-oxa-bicyclo[3.2.1]octa-3,6-dien-2-one are isolated.

後処理

  1. extractionextracted three times with ethyl acetate
  2. dry with materialDrying over sodium sulfate and concentration by evaporation
  3. customFor further purification
  4. customthe dark oil so obtained
  5. customis purified by chromatography over silica gel with 5% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-59a2ab5241494cfbb1d6a0df3482335f
出典データセット
uspto-grants-2010_08
特許番号
US07776888B2

反応ノート

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