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

HRID 2170927ノート

反応式

HRID 2170927 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+].[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]

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

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-260ad74cf85840018cf2ffc733192fb5
出典データセット
uspto-grants-2015_06
特許番号
US09051289B2

反応ノート

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