Benzyl Alcohol → HCID 19080045, 화합물

HRID 964193

반응식

HRID 964193 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 19080045HCID 19080045, 화합물수율 73.6%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-42e4ecca3cde4cb382cfced4daddbcd4
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05767256

연결된 노트

불러오는 중…