Triethylamine → 3-Phenylthio-4-(4-(methylsulfonyl)phenyl)-5h-furan-2-one

HRID 481377

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HRID 481377 반응식
C(N(CC)CC)C.[S:8]([CH2:15][C:16]([OH:18])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=O.C1CCN2C(=NCCC2)CC1>C(#N)C>[C:9]1([S:8][C:15]2[C:16](=[O:18])[O:17][CH2:20][C:21]=2[C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 59541(Phenylthio)acetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

생성물 1

HCID 102691353-Phenylthio-4-(4-(methylsulfonyl)phenyl)-5h-furan-2-one

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

At 0° C., triethylamine (335 μL) was added to a solution of thiophenoxyacetic acid (161 mg) and 2-bromo-l-(4-(methylsulfonyl) phenyl) ethanone (272 mg, WO 9500501, example 9, Step 1) in 5 mL of acetonitrile and the mixture was stirred at 0° C. for 1 h. The reaction mixture was then cooled to -20° C. and DBU (265 μL) was added. The mixture was stirred for 30 min. at -20° C. and was quenched by addition of 1N HCl. The product was extracted with EtOAc, dried over sodium sulfate and partially purified by silica gel chromatography. The impure product was recrystalized from EtOAc/Hexane to afford the title compound as a solid

후처리

  1. temperatureThe reaction mixture was then cooled to -20° C.
  2. stirringThe mixture was stirred for 30 min. at -20° C.
  3. customwas quenched by addition of 1N HCl
  4. extractionThe product was extracted with EtOAc
  5. dry with materialdried over sodium sulfate
  6. custompartially purified by silica gel chromatography
  7. customThe impure product was recrystalized from EtOAc/Hexane

출처 및 근거

ORD 기록
ord-6197c4ee24984d6da99e2e74b559676a
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789413

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