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

HRID 1642
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인쇄 미리보기

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HRID 1642 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매

2
HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0833dde5dcd44e279ff441b2ca2671fd
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05726191

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