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Trifluoroacetic acid → {4-[(1,1-Dimethylethyl)thio]-5-hydroxy-2-pyridinyl}methyl acetate

HRID 639036
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HRID 639036 반응식
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([S:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([O:17]CC2C=CC(OC)=CC=2)=[CH:8][N:7]=1)(=[O:3])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([S:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([OH:17])=[CH:8][N:7]=1)(=[O:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68576335[4-[(1,1-Dimethylethyl)thio]-5-({[4-(methoxy)phenyl]methyl}oxy)-2-pyridinyl]methyl acetate

생성물 1

HCID 68577438{4-[(1,1-Dimethylethyl)thio]-5-hydroxy-2-pyridinyl}methyl acetate수율 83.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of [4-[(1,1-dimethylethyl)thio]-5-({[4-(methoxy)phenyl]methyl}oxy)-2-pyridinyl]methyl acetate (9 g, 24 mmol) in dichloromethane (100 mL) was treated with triethylsilane (3.86 mL, 24 mmol). The reaction mixture was stirred for 10 minutes before adding trifluoroacetic acid (10 mL). The reaction mixture was stirred at room temperature for 3 hours under argon atmosphere. The solvents were evaporated under vacuum. The residue was taken up in dichloromethane and chromatographed on silica gel eluting with 10%-30% ethyl acetate in hexane to afford the product as an oil (5.1 g, 83%); MS (+ve ion electrospray) m/z 256 (MH+).

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours under argon atmosphere
  2. customThe solvents were evaporated under vacuum
  3. customchromatographed on silica gel eluting with 10%-30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-f803601791a347b5a3a5036e038cde2e
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07691850B2

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