Sulfuric Acid → Methyl 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylate

HRID 6972

반응식

HRID 6972 반응식
C(O[C:4](=[O:13])[CH:5]=[C:6](OC)[C:7]([F:10])([F:9])[F:8])C.[C:14]([O:18][CH3:19])(=[O:17])[CH2:15][SH:16].[OH-].[K+].OS(O)(=O)=O>CO.O>[CH3:19][O:18][C:14]([C:15]1[S:16][C:6]([C:7]([F:8])([F:9])[F:10])=[CH:5][C:4]=1[OH:13])=[O:17]

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 16907Methyl ThioglycolateHCID 27588673-Methoxy-4,4,4-trifluoro-2-butenoic acid ethyl ester

생성물 1

HCID 2759855Methyl 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylate수율 91.2%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

A solution of 4,4,4-trifluoro-3-methoxy-but-2-enoic acid ethyl ester (9.6 g, 48.5 mmol) and methyl thioglycolate (4.3 mL, 48.5 mmol) in MeOH (75 mL) is cooled to 5° C. A solution of KOH (3.3 g, 58.2 mmol) in MeOH (75 mL) is then added over 30 min. The reaction mixture is stirred overnight at room temperature. The reaction mixture is then poured over a stirred mixture of ice (75 g), H2O (75 mL) and concentrated H2SO4 (4.5 mL). The mixture is extracted with EtOAc (2×250 mL). The combined extracts are washed with saturated NaHCO3. The washings are back-extracted with EtOAc. The combined organic layers are washed with brine, then dried (Na2SO4), filtered and concentrated to afford the title compound (10 g, 91%) as a brown oil which is used without further purification.

후처리

  1. extractionThe mixture is extracted with EtOAc (2×250 mL)
  2. washThe combined extracts are washed with saturated NaHCO3
  3. extractionThe washings are back-extracted with EtOAc
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3615251532314f45bc7131ceaf9195cd
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084170B2

연결된 노트

불러오는 중…