Dimethyl Sulfoxide → Diethyl 5-(4-fluorobenzoyl)-1,3-benzenedipropanoate

HRID 53329노트

반응식

HRID 53329 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:39])[C:19]2[CH:20]=[C:21]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:22]=[C:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:19]2[CH:20]=[C:21]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:22]=[C:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=2)=[O:39])=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19962357Diethyl 5-[(4-fluorophenyl)hydroxymethyl]-1,3-benzenedipropanoate

생성물 1

HCID 19962378Diethyl 5-(4-fluorobenzoyl)-1,3-benzenedipropanoate수율 94.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Dimethylsulphoxide (16.2 ml) was added dropwise to a stirred solution of oxalyl chloride (11.55 g) in dry dichloromethane (500 ml) at -78° C. under an atmosphere of dry nitrogen. The mixture was stirred for 10 minutes and then a solution of diethyl 5-[(4-fluorophenyl)hydroxymethyl]-1,3-benzenedipropanoate (30.65 g) in dry dichloromethane (150 ml) was added dropwise. The mixture was stirred at -78° C. for 30 minutes, triethylamine (23.03 g) was added, and stirring was continued for a further 10 minutes. The temperature was allowed to rise to room temperature, and the mixture was washed with water. The organic layer was separated, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel. Elution with dichloromethane followed by dichloromethane/methanol (50:1) gave the title compound as an oil (28.92 g), Rf 0.75 (SS 4). Found: C,69.08; H,6.46. C23H25FO5 requires: C,68.98; H,6.29%.

후처리

  1. stirringThe mixture was stirred at -78° C. for 30 minutes
  2. stirringstirring
  3. waitwas continued for a further 10 minutes
  4. customto rise to room temperature
  5. washthe mixture was washed with water
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washElution with dichloromethane

출처 및 근거

ORD 기록
ord-7fd4f784084343b086d6fb22b205e37a
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618941

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