Trifluoroacetic acid → Methyl 4-(thiazol-2-ylmethyl)benzoate

HRID 1039953노트

반응식

HRID 1039953 반응식
O[CH:2]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl.C1(C)C=CC=CC=1>[S:14]1[CH:15]=[CH:16][N:17]=[C:13]1[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 12017830Methyl 4-(hydroxy(thiazol-2-yl)methyl)benzoate

생성물 1

HCID 67249380Methyl 4-(thiazol-2-ylmethyl)benzoate수율 84%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 1140Toluene용매

실험 절차

The product of Step 1 (4.00 g, 16.05 mmol) was taken up in DCE (80 ml) with triethylsilane (25.6 ml, 160 mmol), and trifluoroacetic acid (24.72 ml, 321 mmol) was added. The reaction was stirred at reflux overnight. The reaction was diluted with toluene and evaporated to dryness. The residue was taken back up in EtOAc, washed with aqueous saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated. Flash chromatography (0-50% EtOAc/hexanes) afforded methyl 4-(1,3-thiazol-2-ylmethyl)benzoate (3.13 g, 13.42 mmol, 84% yield) as a pale yellow gum that crystallized upon standing. MS ESI: [M+H]+ m/z 234.1.

후처리

  1. additionwas added
  2. temperatureat reflux overnight
  3. customevaporated to dryness
  4. washwashed with aqueous saturated NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-49934f26ae1746c18225165c0100ed6b
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551984B2

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