Ethyl Acetate → 6-Bromo-8-hydroxy-2,2,4,4-tetramethyl chroman

HRID 2377332노트

반응식

HRID 2377332 반응식
C([O:4][C:5]1[CH:6]=[C:7]([Br:19])[CH:8]=[C:9]2[C:14]=1[O:13][C:12]([CH3:16])([CH3:15])[CH2:11][C:10]2([CH3:18])[CH3:17])(=O)C.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>CO.CCCCCC>[Br:19][C:7]1[CH:8]=[C:9]2[C:14](=[C:5]([OH:4])[CH:6]=1)[O:13][C:12]([CH3:16])([CH3:15])[CH2:11][C:10]2([CH3:18])[CH3:17]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 574242158-Acetoxy-6-bromo-2,2,4,4-tetramethyl chroman2회

생성물 1

HCID 574242146-Bromo-8-hydroxy-2,2,4,4-tetramethyl chroman수율 84%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8058Hexane용매

실험 절차

A solution of 8-acetoxy-6-bromo-2,2,4,4-tetramethyl chroman (Intermediate 16, 1.3 g, 3.98 mmol) in methanol was treated with sodium carbonate (0.8 g, 7.95 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo, the residue was diluted with water and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford a residue that on flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent afforded the title product as an oil (0.95 g, 84%).

후처리

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a residue that on flash column chromatography over silica gel (230-400 mesh)

출처 및 근거

ORD 기록
ord-608c77b5df284771a63942b6fa35b89e
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468391B2

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