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

反応式

HRID 984750 の反応式
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

参加物

8

反応物 3

HCID 280Carbon DioxideHCID 568DibenzofuranHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 4

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
20 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-3b2ff2473bb642a7969c2a0d8e22661c
出典データセット
uspto-grants-2005_03
特許番号
US06867192B1

関連ノート

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