Hydrochloric Acid → 2,6-Dichloro-3-hydroxy-benzaldehyde

HRID 253433노트

반응식

HRID 253433 반응식
C([Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])(C)C)(C)(C)C.C([Li])CCC.CN(C)[CH:24]=[O:25].Cl>O1CCCC1.O>[Cl:16][C:10]1[C:9]([OH:8])=[CH:14][CH:13]=[C:12]([Cl:15])[C:11]=1[CH:24]=[O:25]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 59803885Tert-butyl(2,4-dichlorophenoxy)dimethylsilaneHCID 178418339Butyllithium

생성물 1

HCID 104425302,6-Dichloro-3-hydroxy-benzaldehyde

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To tert-butyl-(2,4-dichloro-phenoxy)-dimethyl-silane (113, 4.00 g, 0.0144 mol) in tetrahydrofuran (50.0 mL), under an atmosphere of nitrogen at −78° C., n-butyllithium (2.50 M in hexane, 6.06 mL) was added slowly. After 30 minutes, N,N-dimethylformamide (1.34 mL, 0.0173 mol) was added to the reaction. After 1 hour, the reaction was allowed to warm to room temperature. 1N HCl (40 mL) was added to the reaction. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a yellow solid (114, 2.0 g, 72.6%).

후처리

  1. waitAfter 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 20% ethyl acetate in hexane
  8. customto give a yellow solid (114, 2.0 g, 72.6%)

출처 및 근거

ORD 기록
ord-13535687cc4c475da14dfd123f61eafb
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872018B2

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