Carbon Dioxide → 8-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid

HRID 984750

반응식

HRID 984750 반응식
C([Li])CCC.[CH:6]1[C:14]2[C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[C:19](=[O:21])=[O:20]>CCCCCC.C1COCC1.C(OCC)C.[OH-].[Na+]>[CH:6]1[C:14]2[C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11][C:10]=2[C:9]([C:19]([OH:21])=[O:20])=[CH:8][CH:7]=1

참가 물질

8

반응물 3

HCID 280Carbon DioxideHCID 568DibenzofuranHCID 178418339Butyllithium

생성물 1

HCID 3028728-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid수율 58%

시약·촉매·용매 4

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
20 °C

실험 절차

A solution of 1.6M n-butyllithium in hexane (18.5 ml) was added dropwise to a stirred solution of dibenzofuran (5.0 g) in anhydrous THF (25 ml) at −78° C. under a nitrogen atmosphere. The resulting suspension was allowed to warm to 20° C. where it was stirred for 3 h. It was then cooled to −78° C. and added to a mixture of excess solid carbon dioxide in diethyl ether (250 ml) under a nitrogen atmosphere. The resulting white suspension was allowed to stand for 1 h at 20° C. and was then diluted with 2M sodium hydroxide (500 ml). The aqueous extract was washed with ether (3×200 ml), acidified to pH 1 with 6M hydrochloric acid and extracted with ethyl acetate (3×200 ml). The combined organic extracts were washed with brine (50 ml), dried over magnesium sulphate and evaporated in vacuo to give the title compound as a white solid (3.64 g, 58%). LCMS: Rt 5.06 min; m/z 213 (MH+).

후처리

  1. temperatureIt was then cooled to −78° C.
  2. waitto stand for 1 h at 20° C.
  3. extractionThe aqueous extract
  4. washwas washed with ether (3×200 ml)
  5. extractionextracted with ethyl acetate (3×200 ml)
  6. washThe combined organic extracts were washed with brine (50 ml)
  7. dry with materialdried over magnesium sulphate
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-3b2ff2473bb642a7969c2a0d8e22661c
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867192B1

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