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

HRID 2295097
ノート
印刷プレビュー

反応式

HRID 2295097 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.[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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4399f650e5344cf29384a69496af2cb1
出典データセット
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05691374

反応ノート

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