Rofecoxib → (2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol

HRID 1437595

반응식

HRID 1437595 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:15][O:14][C:13](=[O:16])[C:12]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CC(C[AlH]CC(C)C)C.[OH-].[Na+]>ClCCl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8](/[C:11](=[C:12](\[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)/[CH2:13][OH:16])/[CH2:15][OH:14])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

참가 물질

5

반응물 3

HCID 5090RofecoxibHCID 14487Diisobutylaluminum hydrideHCID 14798Sodium Hydroxide

생성물 1

HCID 57434773(2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol수율 98.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 110 g of 4-(4-methanesulfonyl-phenyl)-3-phenyl-5H-furan-2-one in 1.5 L of dichloromethane stirred at −78° C., 150 mL of DIBAL was added dropwise. The resulting mixture was warmed to room temperature and stirred overnight. The reaction mixture was then cooled to −78° C., and 1.2 L of 1 M aqueous NaOH was added dropwise. After the addition, the resulting mixture was warmed to room temperature and the organic phase was separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined and dried over Na2SO4. 110 g of the titled compound was obtained after evaporation. 1H NMR (acetone-d6, 500 MHz): δ 7.69 (d, 2H), 7.36 (d, 2H), 7.16-7.05 (m, 5H), 4.66 (d, 2H), 4.63 (d, 2H), 4.19 (t, 1H, OH), 4.17 (t, 1H, OH), 3.04 (s, 3H).

후처리

  1. temperatureThe reaction mixture was then cooled to −78° C.
  2. additionAfter the addition
  3. temperaturethe resulting mixture was warmed to room temperature
  4. customthe organic phase was separated
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-aae632b1cef94b9dac31858548ce79d2
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622502B2

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