Tetrabutylammonium Fluoride → Ethyl 4-ethynyl-3-methylbenzoate

HRID 1259155노트

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HRID 1259155 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[C:13]#[C:14][Si](CC)(CC)CC)[C:5]([O:7][CH2:8][CH3:9])=[O:6].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:13]([C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=1[CH3:1])#[CH:14]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 66874679Ethyl 3-methyl-4-((triethylsilyl)ethynyl)benzoate

생성물 1

HCID 86652354Ethyl 4-ethynyl-3-methylbenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of ethyl 3-methyl-4-((triethylsilyl)ethynyl)benzoate (from the previous step) (1.0 eq.) in THF (0.3 M) at 0° C. was added dropwise 1.0 M TBAF in THF (1.2 eq.). After stirring for 10 minutes at 0° C., the reaction was quenched with saturated aqueous sodium bicarbonate solution. The two phases were separated, and the aqueous layer was extracted with ether. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% ethyl acetate in hexane to give ethyl 4-ethynyl-3-methylbenzoate as a white solid.

후처리

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate solution
  2. customThe two phases were separated
  3. extractionthe aqueous layer was extracted with ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vaccuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

출처 및 근거

ORD 기록
ord-3f557a10b4734d3a96b1a70aefe2c7e8
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466167B2

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