Triethylamine → 3-(4-Methoxyphenylsulfonyl)propenoic acid

HRID 1421519노트

반응식

HRID 1421519 반응식
I[CH:2]([CH2:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)(=[O:9])=[O:8])[C:3]([OH:5])=[O:4].CCN(CC)CC>C(Cl)Cl.Cl>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([S:7]([CH:6]=[CH:2][C:3]([OH:5])=[O:4])(=[O:9])=[O:8])=[CH:11][CH:12]=1

참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 187798602-Iodo-3-(4-methoxyphenylsulfonyl)propionic acid

생성물 1

HCID 538137123-(4-Methoxyphenylsulfonyl)propenoic acid수율 14.3%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매2회

실험 절차

2-Iodo-3-(4-methoxyphenylsulfonyl)propionic acid (4.23 grams, 11.43 mmol) and Et3N (3.22 ml, 2.34 grams, 23.09 mmol) were combined in methylene chloride (150 ml) and stirred overnight at room temperature. The reaction mixture was diluted with 1N hydrochloric acid(aq) (100 ml). The separated aqueous layer was extracted with Et2O (2×). The dried (MgSO4) combined organics were then filtered and concentrated in vacuo to give 2.58 grams of crude product. This was filtered, the filtrate concentrated and the residue taken up in methanol, filtered and the filtrate concentrated to give 1.87 grams of crude product. This was taken up in hot methylene chloride. Fine crystals crashed out. Decanted filtrate. Washed crystals methylene chloride (2×1 ml) (decanted washings). Dried crystals on high vac to give 0.396 grams of 3-(4-Methoxyphenylsulfonyl)propenoic acid as a pale yellow solid (m.p.: 123°-128.5° C.). The filtrate was concentrated to give 1.42 grams of yellow solid which was flash chromatographed (60% EtOAc/hexane/2%/HOAc/0.5% methanol) to give 1.42 grams of 3-(4-Methoxyphenylsulfonyl)propenoic acid. A second chromatography (40% EtOAc/hexane/2%/HOAc/0.5% methanol) gave 0.568 grams of pure 3-(4-Methoxyphenylsulfonyl)propenoic acid.

후처리

  1. extractionThe separated aqueous layer was extracted with Et2O (2×)
  2. dry with materialThe dried (MgSO4)
  3. filtrationcombined organics were then filtered
  4. concentrationconcentrated in vacuo
  5. customto give 2.58 grams of crude product
  6. filtrationThis was filtered
  7. concentrationthe filtrate concentrated
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated
  10. customto give 1.87 grams of crude product
  11. washWashed crystals methylene chloride (2×1 ml) (decanted washings)
  12. customDried crystals on high vac

출처 및 근거

ORD 기록
ord-615d0000e3134b619e4398170ccea560
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077864

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