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Hydrochloric Acid → 5-Hydroxy-4-(4-methanesulfonyl-phenyl)-5-methyl-3-phenyl-5H-furan-2-one

HRID 2295097
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HRID 2295097 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.[C:16]1([CH2:22][C:23]([OH:25])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1CCN2C(=NCCC2)CC1.[O:37]=O.Cl>CC#N.[Cl-].[Na+].O.CCN(CC)CC>[OH:37][C:2]1([CH3:15])[O:24][C:23](=[O:25])[C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 977OxygenHCID 999Phenylacetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 132078392-Bromo-1-[4-(methanesulfonyl)phenyl]propan-1-one

생성물 1

HCID 214727535-Hydroxy-4-(4-methanesulfonyl-phenyl)-5-methyl-3-phenyl-5H-furan-2-one

시약·촉매·용매

3
HCID 6342Acetonitrile용매HCID 8471Triethylamine용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of 2-bromo-1-(4-methylsulfonylphenyl)-propan-1-one (prepared using the methodology of WO 9500501, Ex. 9 Step 1) (8.7 g) and phenyl acetic acid (5 g) in 150 mL of CH3CN was treated with 8.5 mL of Et3N. The reaction mixture was stirred overnight at r.t. and then 12 mL of DBU was added dropwise over 2 min. After stirring for 1 h at r.t. O2 was bulbed into the mixture until it became colorless (in 45 min.). The reaction mixture was then poured into a solution of 80 mL 1N HCl and 100 mL of brine, and extracted with 500 mL of 1:1 EtOAc/hexane. The extract was dried over MgSO4, filtered and concentrated. The crude product was swished from 1:4 EtOAc/hexane (200 mL) to give 7.2 g of the title product as a white solid.

후처리

  1. customprepared
  2. stirringAfter stirring for 1 h at r.t
  3. custom(in 45 min.)
  4. extractionextracted with 500 mL of 1:1 EtOAc/hexane
  5. dry with materialThe extract was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4399f650e5344cf29384a69496af2cb1
출처 데이터셋
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05691374

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