Tetrabutylammonium Fluoride → 4-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoic acid

HRID 265804노트

반응식

HRID 265804 반응식
[OH:1][C:2]1(C(OCC)=O)[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[C:7](C)=[C:6]([C:15]#[C:16][C:17]3[CH:31]=[CH:30][C:20]([C:21]([O:23]CC[Si](C)(C)C)=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.[F-].C([N+](CC[CH2:53][CH3:54])(CCCC)CCCC)CCC>C1COCC1>[OH:1][C:2]1([CH2:20][C:21]([O:23][CH2:53][CH3:54])=[O:22])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:15]#[C:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:30][CH:31]=3)[CH:5]=[CH:4][C:3]1=2

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 70151178Trimethylsilylethyl 4-((5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxy-methylnaphth-2-yl)ethynyl]benzoate2회

생성물 1

HCID 183145664-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 0.25 g (0.49 mmol) of trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxy-methylnaphth-2-yl)ethynyl]benzoate (Compound 117) in 5 ml of dry THF (flushed with argon) was added 1.48 ml (1.5 mmol) of tetrabutylammonium fluoride (1M solution in THF). The reaction mixture was stirred at room temperature for 12 hours, concentrated in vacuo to an oil and slowly diluted with water. The solution was acidified to pH 4 with 10% HCl and extracted with Et2O. The organic layer was dried over Na2SO4, concentrated in vacuo to an oil and purified by flash chromatography (silica, 90% EtOAc-hexane) to give the title compound as a white solid.

후처리

  1. concentrationconcentrated in vacuo to an oil
  2. additionslowly diluted with water
  3. extractionextracted with Et2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo to an oil
  6. custompurified by flash chromatography (silica, 90% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-49bf71ba444d4cf78fc5ebe09eba336c
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648514

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