4-Bromoanisole → (4-Methoxyphenyl)-2-pyridinylmethanone

HRID 473621노트

반응식

HRID 473621 반응식
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5].Br[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>C1COCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[O:5])=[CH:15][CH:16]=1

참가 물질

4

반응물 2

HCID 77304-BromoanisoleHCID 11829796N-Methoxy-N-methylpicolinamide

생성물 1

HCID 80559(4-Methoxyphenyl)-2-pyridinylmethanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of pyridine-2-carboxylic acid methoxy-methyl-amide (10.0 g, 0.060 mol) in anhydrous THF (150 mL) at −78° C. was added freshly prepared Grignard reagent of 4-bromo anisole (20.0 g, 0.106 mol). The reaction mixture was allowed to warm to room temperature. Reaction mixture was quenched with saturated ammonium chloride (100 mL) and extracted with ethyl acetate (2×200 mL). Organic layer was dried over sodium sulphate and concentrated. Purification by 100-200-mesh sized silica gel column with 0-20% EtoAc:Hexane as eluent provided the product.

후처리

  1. customReaction mixture
  2. customwas quenched with saturated ammonium chloride (100 mL)
  3. extractionextracted with ethyl acetate (2×200 mL)
  4. dry with materialOrganic layer was dried over sodium sulphate
  5. concentrationconcentrated
  6. customPurification by 100-200-mesh sized silica gel column with 0-20% EtoAc
  7. customHexane as eluent provided the product

출처 및 근거

ORD 기록
ord-1e8b74a41cec4251ab86e8818e0d05a7
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637500B2

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