Thionyl Chloride → Ethyl 2-[4-(chloromethyl)phenyl]-1,3-oxazole-4-carboxylate

HRID 1716825노트

반응식

HRID 1716825 반응식
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:3][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[CH:9][CH:8]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 46834789Ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate

생성물 1

HCID 46834790Ethyl 2-[4-(chloromethyl)phenyl]-1,3-oxazole-4-carboxylate수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of methylene chloride at −10° C. and excess thionyl chloride was added portionwise ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate (1 eq) and the resulting mixture was stirred at room temperature for 3 h. The solvent was removed and the residue was azeotroped with toluene, dissolved in methylene chloride, washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and evaporated to give a yield of 96% of the product as white crystals; m.p. 115-117° C. 1H NMR (300 MHz, CDCl3, δ): 8.28 (s, 1H), 8.12 (d, 2H, J=8.5 Hz), 7.50 (d, 2H, J=8.5 Hz), 4.62 (s, 2H), 4.43 (m, 2H, J=7.4 Hz), 1.41 (t, 3H, J=7.4 Hz).

후처리

  1. customThe solvent was removed
  2. customthe residue was azeotroped with toluene
  3. dissolutiondissolved in methylene chloride
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-c2042fb571624d4381a6a957afff6cec
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803825B2

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