Acetic Acid → HCID 21182319, 화합물

HRID 1386611노트

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HRID 1386611 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2C=C[C:11]([CH2:14][CH2:15][CH2:16]CCCC)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:21]([Li])[CH2:22]CC.[C:26]([O:33]CC)(=O)[C:27]([O:29]CC)=O.C(O)(=O)C>O1CCCC1.C(OCC)C.CCCCCC.C(OCC)(=O)C.O>[CH2:21]([C:27](=[O:29])[C:26]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:14][CH2:15][CH3:16])=[CH:6][CH:7]=1)=[O:33])[CH3:22]

참가 물질

10

반응물 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 6187104-Bromo-4'-heptylbiphenylHCID 178418339Butyllithium

생성물 1

HCID 21182319HCID 21182319, 화합물

시약·촉매·용매 5

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

To a stirred solution of 4-bromo-4′-n-heptylbiphenyl (2.71 g) in tetrahydrofuran (100 ml) was added dropwise a solution of n-butyllithium in a mixture of diethyl ether and n-hexane (1.6M, 5.1 ml) at −78° C. After stirring at −78° C. for 30 minutes, the resultant mixture was added to a solution of diethyl oxalate (3.4 ml) in tetrahydrofuran (50 ml) at −78° C. The resultant mixture was allowed to warm to 0° C. for about 1 hour, and to the mixture was added acetic acid (0.5 ml). Evaporation gave a residue which was taken up into a mixture of water and ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate. Evaporation gave a residue which was chromatographed on silica gel (200 ml) eluting with a mixture of n-hexane and ethyl acetate (10:0-95:5, V/V) to give 1-Ethyl-2-(4-n heptylphenyl)ethanedione (2.23 g).

후처리

  1. temperatureto warm to 0° C. for about 1 hour
  2. customEvaporation
  3. customgave a residue which
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation
  8. customgave a residue which
  9. customwas chromatographed on silica gel (200 ml)
  10. washeluting with a mixture of n-hexane and ethyl acetate (10:0-95:5, V/V)

출처 및 근거

ORD 기록
ord-005967bc974c4aea82b5d793ff52363f
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265536B1

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