Carbon Dioxide → 3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoic acid

HRID 1642

反応式

HRID 1642 の反応式
[C:1]12([C:11]3[CH:24]=[C:23](Br)[CH:22]=[CH:21][C:12]=3[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([Li])CCC.[C:31](=[O:33])=[O:32].[Cl-].[NH4+].Cl>O1CCCC1.CCCCCC>[C:1]12([C:11]3[CH:24]=[C:23]([CH:22]=[CH:21][C:12]=3[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:31]([OH:33])=[O:32])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

参加物

8

反応物 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 107883163-(1-Adamantyl)-4-(t-butyldimethylsilyloxy)bromobenzeneHCID 178418339Butyllithium

生成物 1

HCID 136335593-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

9.3 g of (2-adamantan-1-yl-4-bromo-phenoxy)-tert-butyl-dimethylsilane were dissolved in 120 ml of absolute tetrahydrofuran and treated dropwise at -78° C. with 15.5 ml of a 1.6 molar solution of n-butyl-lithium in hexane. After stirring at -78° C. for 1.5 hours, a vigorous stream of carbon dioxide was introduced for one hour. Subsequently, the reaction mixture was firstly poured into ice-cold, saturated, aqueous ammonium chloride solution, acidified cautiously to pH 3 with cold 2N hydrochloric acid and extracted with ethyl acetate. After washing once with water, drying over sodium sulfate and evaporation there was obtained a white, crystalline mass which was recrystallized from ethyl acetate and gave 7 g of 3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoic acid, m.p. 250°-252° C.

後処理

  1. additionSubsequently, the reaction mixture was firstly poured into ice-cold
  2. extractionextracted with ethyl acetate
  3. washAfter washing once with water
  4. dry with materialdrying over sodium sulfate
  5. customevaporation there
  6. customwas obtained a white, crystalline mass which
  7. customwas recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-0833dde5dcd44e279ff441b2ca2671fd
出典データセット
uspto-grants-1998_03
特許番号
US05726191

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