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

HRID 502915노트

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HRID 502915 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-59a2ab5241494cfbb1d6a0df3482335f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776888B2

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