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

HRID 639036
ノート
印刷プレビュー

反応式

HRID 639036 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-f803601791a347b5a3a5036e038cde2e
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07691850B2

反応ノート

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