Ethyl 3-(tributylsilyloxy)picolinate → 2-(4-Fluorobenzoyl)-3-(tributylsilyloxy)pyridine

HRID 986974노트

반응식

HRID 986974 반응식
[CH2:1]([Si:5]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])[O:6][C:7]1[C:8]([C:13]([O:15]CC)=O)=[N:9][CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH3:4].[F:26][C:27]1[CH:32]=[CH:31][C:30]([Mg]Cl)=[CH:29][CH:28]=1>O1CCCC1>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:13]([C:8]2[C:7]([O:6][Si:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:15])=[CH:29][CH:28]=1

참가 물질

4

반응물 2

HCID 22987980Ethyl 3-(tributylsilyloxy)picolinateHCID 178505844HCID 178505844, 화합물

생성물 1

HCID 229879642-(4-Fluorobenzoyl)-3-(tributylsilyloxy)pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of ethyl 3-(tributylsilyloxy)picolinate (19 g, 35 mmol) in tetrahydrofuran (100 ml) was cooled to 0° C. and 4-fluorophenylmagnesium chloride (52 ml, 1.0 M in tetrahydrofuran) was added dropwise. After 30 min., the reaction mixture was quenched with water and the product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification on a silica gel column using ethyl acetate-hexane (2:98) as the eluant gave 2-(4-fluorobenzoyl)-3-(tributylsilyloxy)pyridine (3.75 g).

후처리

  1. customthe reaction mixture was quenched with water
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification on a silica gel column

출처 및 근거

ORD 기록
ord-dfd6cafa8a334d39b6085f772452719f
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630485B2

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