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

HRID 1269345

反応式

HRID 1269345 の反応式
[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]

参加物

5

反応物 3

HCID 5090RofecoxibHCID 14487Diisobutylaluminum hydrideHCID 14798Sodium Hydroxide

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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 M Hz): δ 7.69 (d, 2 H), 7.36 (d, 2 H), 7.16–7.05 (m, 5 H), 4,66 (d, 2 H), 4.63 (d, 2 H), 4.19 (t, 1 H, OH), 4.17 (t, 1 H. OH), 3.04 (s, 3 H).

後処理

  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

出典と根拠

ORDレコード
ord-a0d1798d1a4a4937b9d1bbf49333574c
出典データセット
uspto-grants-2007_04
特許番号
US07199154B2

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