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

HRID 429203노트

반응식

HRID 429203 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-d954b17dc7fb47e3bee2a80ca170b2e4
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316464B1

반응 노트

불러오는 중…