Water → Rofecoxib

HRID 357232노트

반응식

HRID 357232 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]#[CH:18])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CCN(CC)CC.C1[CH2:30][O:29][CH2:28]C1.[OH2:31]>>[C:15]1([C:16]2[C:28](=[O:31])[O:29][CH2:30][C:11]=2[C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=2)[CH:14]=[CH:13][CH:12]=[CH:17][CH:18]=1

참가 물질

5

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 184001882-(4-(Methylsulfonyl)phenyl)phenylacetylene

생성물 1

HCID 5090Rofecoxib

실험 절차

Into a 20 ml glass ampule are added 1 g of 2-(4-(methylsulfonyl)phenyl)phenylacetylene, 20 mg of Rh4 (CO)12, 1.5 g of Et3N, 10 ml of THF, 1 ml of water under nitrogen atmosphere, and the ampule is placed in a 100-ml stainless steel autoclave. The reaction system is flushed three times with CO then charged at room temperature to a initial CO pressure of 100 atm. The reaction is carried at 100° C. for 5 h. The solution is then diluted with 50 ml of benzene and washed with brine, 1N HCl. The benzene solution is dried over Na2SO4, and concentrated. The crude products are separated by column chromatography on silica gel eluted with 2:1 EtOAc/hexane to give the title compound and its regioisomer.

후처리

  1. customThe reaction system is flushed three times with CO
  2. additionthen charged at room temperature to a initial CO pressure of 100 atm
  3. additionThe solution is then diluted with 50 ml of benzene
  4. washwashed with brine, 1N HCl
  5. dry with materialThe benzene solution is dried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude products are separated by column chromatography on silica gel
  8. washeluted with 2:1 EtOAc/hexane

출처 및 근거

ORD 기록
ord-4c61b74c0d1544e3994031dd0fcfd63b
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840746

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