2,2-Dimethylchroman → 2,2-Dimethylchroman-8-carboxylic acid

HRID 864372

反応式

HRID 864372 の反応式
C([Li])CCC.[CH3:6][C:7]1([CH3:17])[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8]1.[C:18](=[O:20])=[O:19].C(OCC)C>CCCCCC.C(OCC)C>[CH3:6][C:7]1([CH3:17])[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([C:18]([OH:20])=[O:19])[CH:11]=[CH:12][CH:13]=2)[O:8]1

参加物

6

反応物 3

HCID 1369362,2-DimethylchromanHCID 86742199Dry ice diethyl etherHCID 178418339Butyllithium

生成物 1

HCID 130516922,2-Dimethylchroman-8-carboxylic acid

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

実験手順

To a solution of 1.6M n-butyllithium in hexane and 150 ml of diethyl ether were added a solution of 27 g of 2,2-dimethylchroman in diethyl ether over a one hour period at room temperature. The solution was then heated at reflux 160 minutes, cooled, and poured into dry ice/diethyl ether. The mixture was allowed to come to room temperature, poured into ice water, and layers separated. The organic layer was washed with water, dried over sodium sulfate, and concentrated in vacuo to provide 21 g of solid. The aqueous layer was acidified and the resulting precipitate extracted into diethyl ether/ethyl acetate. The organic extract was washed with water, dried over sodium sulfate, and concentrated in vacuo to provide 9 g of solid. The two isolated solids were combined and chromatographed over silica gel eluting with 10% ethyl acetate in toluene. The appropriate fractions were combined and concentrated in vacuo to provide 9.8 g of the desired title intermediate, m.p. 90°-92° C.

後処理

  1. temperatureThe solution was then heated
  2. temperatureat reflux 160 minutes
  3. temperaturecooled
  4. customto come to room temperature
  5. customseparated
  6. washThe organic layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-02106d7114ca4a6dbc8eb3d4d8df640d
出典データセット
uspto-grants-1996_10
特許番号
US05563148

関連ノート

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