Dimethyl Sulfoxide → Methyl benzo(b)thiophene-2-carboxylate

HRID 343881

반응식

HRID 343881 반응식
CS(C)=O.F[C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.C(N(CC)CC)C.[C:21]([O:25][CH3:26])(=[O:24])[CH2:22][SH:23]>ClCCl.CCCCCC>[S:23]1[C:22]([C:21]([O:25][CH3:26])=[O:24])=[CH:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]1=2

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 67970o-Fluorobenzaldehyde

생성물 1

HCID 2800344Methyl benzo(b)thiophene-2-carboxylate수율 85%

시약·촉매·용매 1

HCID 21226440Methylenechloride Hexane용매

실험 절차

A 100 ml 3-necked round-bottomed flask, reflux condenser, thermometer adapter, gas inlet, and Teflon stirrer were oven-dried for 12 hours at 160° C. The apparatus was rapidly assembled, fitted with a thermometer, flushed with dry nitrogen gas, sealed with rubber septa and allowed to cool to room temperature. The cooled reaction flask was charged with anhydrous dimethyl sulfoxide (40 ml), 2-fluorobenzaldehyde (4.44 g, 31.53 mmole), anhydrous triethylamine (2.5 equivalents, 78.83 mmole, 7.976 g, 11 ml) and methyl thioglycolate (1.1 equivalents, 3.681 g, 3.10 ml, 34.68 mmole) and heated to 75° C. with rapid stirring. The progress of the reaction was monitored by TLC (silica, 10% dichloromethane-hexane, UV visualization). After 18 hours the reaction mixture was cooled to room temperature and poured onto an ice/water bath (250 ml). The resulting slurry was stirred for 20 minutes, filtered, washed with cold water (2×100 ml) and dried in vacuo to give 5.136 g (85%) of methyl benzo[b]thiophene-2-carboxylate.

후처리

  1. temperatureA 100 ml 3-necked round-bottomed flask, reflux condenser, thermometer adapter, gas inlet, and Teflon stirrer
  2. customwere oven-dried for 12 hours at 160° C
  3. customfitted with a thermometer
  4. customflushed with dry nitrogen gas
  5. customsealed with rubber septa
  6. customThe cooled reaction flask
  7. temperatureheated to 75° C. with rapid stirring
  8. temperatureAfter 18 hours the reaction mixture was cooled to room temperature
  9. additionpoured onto an ice/water bath (250 ml)
  10. filtrationfiltered
  11. washwashed with cold water (2×100 ml)
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-514c7e6eb48741a78599d2c06fda833d
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05863936

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