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

HRID 55297노트

반응식

HRID 55297 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 53970358Methyl 2-(4-ethynylphenyl)acetate수율 79.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-09e6834678d94284b7b9a59bc53bfcd3
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624943

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