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

HRID 237451노트

반응식

HRID 237451 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+].CS(O[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)(=O)=O>CN1CCCC1=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]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

To a solution of 4-bromo-3,5-dimethylphenol (3 g) in N-methyl-pyrrolidone (10 mL) is slowly added Cs2CO3 (9.7 g) and tetrahydro-2H-pyran-4-yl methanesulfonate (5.4 g). The mixture is heated for 3 hours at 140° C. After cooling to room temperature the mixture is partitioned between saturated aqueous Na2CO3 solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (MgSO4). The solvents are evaporated and the residue is purified by HPLC on reversed phase to give the title compound. Yield: 1.2 g; LC (method 4): tR=1.83 min.

후처리

  1. temperatureAfter cooling to room temperature the mixture
  2. customis partitioned between saturated aqueous Na2CO3 solution and ethyl acetate
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried (MgSO4)
  5. customThe solvents are evaporated
  6. customthe residue is purified by HPLC on reversed phase

출처 및 근거

ORD 기록
ord-681e0752718944dfa4ac8743b00107c0
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642585B2

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