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

HRID 237451ノート

反応式

HRID 237451 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-681e0752718944dfa4ac8743b00107c0
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

反応ノート

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