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Carbon Dioxide → 2,5-Bis[(tetrahydropyran-2-yl)oxymethyl]benzoic acid

HRID 1766853
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인쇄 미리보기

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HRID 1766853 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH:10]=[CH:9][C:8]=1[CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1.[C:29](=[O:31])=[O:30].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[O:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]1[O:22][CH2:21][C:8]1[CH:9]=[CH:10][C:11]([CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:12][C:7]=1[C:29]([OH:31])=[O:30]
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참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 211104512-Bromo-1,4-bis[(tetrahydropyran-2-yl)oxymethyl]benzeneHCID 178418339Butyllithium

생성물 1

HCID 211104372,5-Bis[(tetrahydropyran-2-yl)oxymethyl]benzoic acid수율 50%

시약·촉매·용매 3

HCID 8028
Tetrahydrofuran
용매
HCID 8058Hexane용매
HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

n-Butyllithium (1.57 M hexane solution; 8.33 ml, 13.1 mmol) was added dropwise to a solution of 2-bromo-1,4-bis[(tetrahydropyran-2-yl)oxymethyl]benzene (3.55 g, 9.22 mmol) obtained from Example 1-(2) in tetrahydrofuran (30 ml) with stirring at −78° C. After the mixture was stirred at the same temperature for 20 minutes, carbon dioxide gas was introduced thereto for 40 minutes. The resulting mixture was stirred at the same temperature for 1 hour, and then the reaction was stopped by addition of a saturated aqueous solution of ammonium chloride. The mixture was warmed to 0° C., and then the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to afford the residue. The residue was subjected to chromatography on a silica gel (100 g) column (eluent; ethyl acetate:hexane=1:3) to give the title compound (1.63 g, 50% yield) as a colorless oil.

후처리

  1. stirringAfter the mixture was stirred at the same temperature for 20 minutes
  2. stirringThe resulting mixture was stirred at the same temperature for 1 hour
  3. temperatureThe mixture was warmed to 0° C.
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto afford the residue

출처 및 근거

ORD 기록
ord-cbea3d04070e40bda3839db7f1e42926
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07230023B2

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