Tetrabutylammonium Fluoride → Ethyl 4-ethynyl-3-methylbenzoate

HRID 340287ノート

反応式

HRID 340287 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 86652354Ethyl 4-ethynyl-3-methylbenzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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 vacuo. 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.

後処理

  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 vacuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

出典と根拠

ORDレコード
ord-b311b498ddfa48e69445cff7859fc390
出典データセット
uspto-grants-2014_11
特許番号
US08895577B2

反応ノート

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