Cesium carbonate → 4-(4-Bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran

HRID 2170927노트

반응식

HRID 2170927 반응식
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].[O:17]1[CH2:22][CH2:21][CH:20](OS(C)(=O)=O)[CH2:19][CH2:18]1>CN1C(=O)CCC1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:20]2[CH2:21][CH2:22][O:17][CH2:18][CH2:19]2)=[CH:4][C:3]=1[CH3:10]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 11344352Oxan-4-yl methanesulfonate

생성물 1

HCID 866971154-(4-Bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
140 °C

실험 절차

Reaction under argon atmosphere: 3.0 g (15 mmol) of 4-bromo-3,5-dimethylphenol are dissolved in 20.0 ml NMP. 20.0 g (61.4 mmol) of cesium carbonate and 11.0 g (61.0 mmol) of methanesulfonic acid tetrahydropyran-4-yl ester are added. The reaction mixture is stirred at 140° C. for 4 h. The solvent is evaporated. The residue is diluted with EtOAc and washed with water and brine. The organic layer is dried and the solvent is evaporated. The residue is chromatographed on silica gel (CH/EtOAc=99/1→60/40) to give the title compound. Yield: 4.0 g; LC (method 1): tR=1.15 min; Mass spectrum (ESI+): m/z=285 [M+H]+.

후처리

  1. customReaction under argon atmosphere
  2. customThe solvent is evaporated
  3. additionThe residue is diluted with EtOAc
  4. washwashed with water and brine
  5. customThe organic layer is dried
  6. customthe solvent is evaporated
  7. customThe residue is chromatographed on silica gel (CH/EtOAc=99/1→60/40)

출처 및 근거

ORD 기록
ord-260ad74cf85840018cf2ffc733192fb5
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051289B2

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