Benzyl Alcohol → 2,2-Dimethyl-4-benzyloxycarbonylbutyric acid

HRID 964193

反応式

HRID 964193 の反応式
[CH3:1][C:2]1([CH3:10])[CH2:8][CH2:7][C:6](=[O:9])[O:5][C:3]1=[O:4].[CH2:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)(CCC(O)=O)C(O)=O.OS(O)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][C:2]([CH3:10])([CH2:8][CH2:7][C:6]([O:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:3]([OH:5])=[O:4]

参加物

8

反応物 4

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 126812,2-Dimethylglutaric acidHCID 76247Dihydro-3,3-dimethyl-2H-pyran-2,6(3H)-dione

生成物 1

HCID 190800452,2-Dimethyl-4-benzyloxycarbonylbutyric acid収率 73.6%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 3 g (0.021 mol) of 2.2-dimethylglutaric anhydride, 2.0 ml (0.019 mol) of benzyl alcohol in 10 ml of CH2Cl2 was added 100 mg of DMAP and 3.4 ml of pyridine. The resulting solution was stired at room temperature for 4 h. After additional 2.2-dimethyl-glutaric acid (0.7 g, 4.9 mmol) was added, the mixture continued to be stirred overnight, then poured into 0.5M H2SO4 (aq.) solution and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4 and filtered. Concentration followed by purification by flash chromatography on silica gel using EtOAc/hexane (1:1) as the irrigant gave 3.5 g of desired product in 66% yield and 1.2 g of isomer in 23% yield.

後処理

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationConcentration
  6. customfollowed by purification by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-42e4ecca3cde4cb382cfced4daddbcd4
出典データセット
uspto-grants-1998_06
特許番号
US05767256

関連ノート

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