3-Hydroxybenzyl alcohol → 3-[(6-Methyl-2-pyridinyl)oxy]benzenemethanol

HRID 1666388

反応式

HRID 1666388 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.F[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:17][C:13]1[N:12]=[C:11]([O:9][C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=[CH:7][CH:6]=2)[CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 1023-Hydroxybenzyl alcoholHCID 10796Cesium carbonateHCID 960902-Fluoro-6-methylpyridine

生成物 1

HCID 668761143-[(6-Methyl-2-pyridinyl)oxy]benzenemethanol収率 64%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

3-Hydroxymethyl-phenol (3.69 g, 29.7 mmol), 2-fluoro-6-methyl-pyridine (3.00 g, 27 mmol,) and cesium carbonate (9.68 g, 29.7 mmol) were suspended in dimethylsulfoxide (25 mL) and heated to 110° C. After stirring for 16 h, the reaction was partitioned between water (250 mL) and ethyl acetate (250 mL). The organic layer was separated and the aqueous was extracted again with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (10-50%, EtOAc:heptane) to afford the title compound (3.72 g, 64% yield) as an off-white solid.

後処理

  1. customthe reaction was partitioned between water (250 mL) and ethyl acetate (250 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous was extracted again with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (10-50%, EtOAc:heptane)

出典と根拠

ORDレコード
ord-9ea66b4dec644cb4a889b38fdfe4acff
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

関連ノート

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