Pyridine → 3-Hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone

HRID 376347

反応式

HRID 376347 の反応式
[OH:1][C:2]([CH3:16])([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.N1C=CC=CC=1.C([O:26][CH2:27][C:28](Cl)=[O:29])(=O)C.C1CCN2C(=NCCC2)CC1>CC#N.CCOC(C)=O.O.[Cl-].[Na+].O.C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:15][C:2]1([CH3:16])[O:1][C:27](=[O:26])[C:28]([OH:29])=[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

10

反応物 4

HCID 1049PyridineHCID 26297Acetoxyacetyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2 回HCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

生成物 1

HCID 155422043-Hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone収率 42.9%

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒HCID 21877217Toluene methylene chloride溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a 0° C. solution of the alcohol of Example 1, Step 3 (14.0 g, 57.8 mmol) in CH3CN (180 mL) were added pyridine (10.0 mL) and acetoxyacetyl chloride (12.7 g, 93.0 mmol) after a period of 7 h at r.t., DBU (15.0 mL) was added to the reaction mixture. After a period of 1 h at 80° C., a second portion of DBU (20.0 mL) was added. The reaction mixture was kept at 80° C. for 18 h. The reaction mixture allowed to cool to r.t. The mixture was diluted with EtOAc (500 mL) and H2O (500 mL) and acidified with 6NHCl. After the addition of brine (100 mL), the aqueous phase was extracted 2 times with EtOAc. The organic phase was evaporated to provide a brown residue. To the solid was added a 2:1 mixture of CH2Cl2 -toluene (150 mL). The solid was filtered and washed with CH2Cl2 -toluene to provide 7.0 g of the title compound.

後処理

  1. waitThe reaction mixture was kept at 80° C. for 18 h
  2. extractionthe aqueous phase was extracted 2 times with EtOAc
  3. customThe organic phase was evaporated
  4. customto provide a brown residue
  5. additionTo the solid was added
  6. filtrationThe solid was filtered
  7. washwashed with CH2Cl2 -toluene

出典と根拠

ORDレコード
ord-e4b5878b53194adaa89a59d653b767ae
出典データセット
uspto-grants-2000_02
特許番号
US06020343

関連ノート

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