Tetrabutylammonium Fluoride → Methyl 2-(4-ethynylphenyl)acetate

HRID 55297ノート

反応式

HRID 55297 の反応式
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si](C)(C)C)=[CH:7][CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[CH:12])=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 54516793Methyl 2-(4-(2-(trimethylsilyl)ethynyl)phenyl)acetate

生成物 1

HCID 53970358Methyl 2-(4-ethynylphenyl)acetate収率 79.2%

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

A solution of 10 g of 4-(2-trimethylsilylethinyl)-phenylacetic acid methyl ester in 950 ml of tetrahydrofuran is mixed at 0° C. with 45 ml of a 1-molar solution of tetrabutylammonium fluoride in tetrahydrofuran. The reaction mixture is stirred for 15 minutes at 0° C. and for 2 hours at room temperature and then concentrated by evaporation. The residue is spread between water and ethyl acetate, the organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-7% ethyl acetate. 5.6 g of 4-ethinylphenylacetic acid methyl ester is obtained as oily crude product.

後処理

  1. concentrationconcentrated by evaporation
  2. customthe organic phase is dried on sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed on silica gel with hexane/0-7% ethyl acetate

出典と根拠

ORDレコード
ord-09e6834678d94284b7b9a59bc53bfcd3
出典データセット
uspto-grants-1997_04
特許番号
US05624943

反応ノート

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