Acetic Acid → 6-bromo-2,2-dimethyl-3-methylene-2,3-dihydro-4H-chromen-4-one

HRID 873734

반응식

HRID 873734 반응식
CN(C)CN(C)C.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]2=[O:21].[C:22](O)(=O)C.C(OC(=O)C)(=O)C>O1CCCC1>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:19])([CH3:20])[C:13](=[CH2:22])[C:12]2=[O:21]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7918Acetic AnhydrideHCID 147553646-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

생성물 1

HCID 867242786-bromo-2,2-dimethyl-3-methylene-2,3-dihydro-4H-chromen-4-one수율 87.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

N,N,N′,N′-tetramethylmethanediamine (4.8 g, 47 mmol) was added to a solution of 6-bromo-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (3.0 g, 12 mmol) and acetic acid (0.67 ml, 12 mmol) in tetrahydrofuran (43 ml), and the mixture was stirred at 70° C. for 24 hours. To the mixture was added acetic anhydride (4.4 ml, 47 mmol), and the mixture was stirred at 70° C. for 4 hours and concentrated in vacuo. The residue was directly purified by silica gel column chromatography (hexane/ethyl acetate=20:1) to afford 6-bromo-2,2-dimethyl-3-methylene-2,3-dihydro-4H-chromen-4-one (2.8 g).

후처리

  1. stirringthe mixture was stirred at 70° C. for 4 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was directly purified by silica gel column chromatography (hexane/ethyl acetate=20:1)

출처 및 근거

ORD 기록
ord-f8f2219a3ef44bf1b910af67ef872ac4
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975415B2

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