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

HRID 376343

반응식

HRID 376343 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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 aqueous 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.

후처리

  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 aqueous HCl, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated under vacuum

출처 및 근거

ORD 기록
ord-6995c775a8d24ed3ad37503f6175cb95
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020343

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