Triethylamine → 5-Hydroxy-4-(4-methanesulfonyl-phenyl)-5-methyl-3-phenylsulfanyl-5H-furan-2-one

HRID 481382

反応式

HRID 481382 の反応式
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.[S:16]([CH2:23][C:24]([OH:26])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.BrC(Br)=[O:36].C1CCN2C(=NCCC2)CC1>C(#N)C>[OH:36][C:2]1([CH3:15])[O:25][C:24](=[O:26])[C:23]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:3]1[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 59541(Phenylthio)acetic acidHCID 79057Carbonyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 132078392-Bromo-1-[4-(methanesulfonyl)phenyl]propan-1-one

生成物 1

HCID 154615225-Hydroxy-4-(4-methanesulfonyl-phenyl)-5-methyl-3-phenylsulfanyl-5H-furan-2-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a mixture of 2-bromo-1-(4-(methylsulfonyl)phenyl) propan-1-one (6.0 g, 20.6 mmol) and thiophenoxyacetic acid (3.8 g, 22.6 mmol) in acetonitrile (60 mL) was added triethylamine (4.0 mL, 28.8 mmol). The mixture was stirred at r.t. for 3 h. T.L.C. showed no bromoketone remaining and DBU (4.0 mL) was added. The mixture was stirred at r.t. for 1 h., then air was bubbled through the mixture for another hour. After dilution with water, the mixture was extracted with EtOAc. The EtOAc extract was washed with 1N aquous HCl, brine, dried over MgSO4, filtered and the solvent evaporated under vacuum. The residue was swished in Et2O to give the title compound (6.0 g) as a pale yellow powder.

後処理

  1. additionwas added
  2. stirringThe mixture was stirred at r.t. for 1 h.
  3. customair was bubbled through the mixture for another hour
  4. extractionAfter dilution with water, the mixture was extracted with EtOAc
  5. extractionThe EtOAc extract
  6. washwas washed with 1N aquous HCl, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated under vacuum

出典と根拠

ORDレコード
ord-fce878e906e94d54a196e76b31ab632d
出典データセット
uspto-grants-1998_08
特許番号
US05789413

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