Dimethyl Sulfoxide → 3-(3-Chlorophenyl)-3-methylbutan-2-one

HRID 1627353노트

반응식

HRID 1627353 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([C:18]([CH3:23])([CH3:22])[CH:19]([OH:21])[CH3:20])[CH:15]=[CH:16][CH:17]=1.CCN(CC)CC>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([C:18]([CH3:23])([CH3:22])[C:19](=[O:21])[CH3:20])[CH:15]=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 667407143-(3-Chlorophenyl)-3-methylbutan-2-ol

생성물 1

HCID 242739623-(3-Chlorophenyl)-3-methylbutan-2-one수율 99.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of oxalyl chloride (3.4 mL, 40 mmol, 2 eq) in CH2Cl2 (100 mL) at −78° C. was added DMSO (4.9 mL, 70 mmol, 3.5 eq) dropwide. After stirring 1 h, the reaction mixture was treated dropwise with a solution of 3-(3-chlorophenyl)-3-methylbutan-2-ol (3.98 g, 20 mmol) in CH2Cl2 (100 mL). After stirring 1 h, Et3N (13.9 mL, 100 mmol, 5 eq) was added to the reaction mixture and the resulting mixture was slowly warmed to room temperature. The reaction mixture was partitioned in CH2Cl2 and water. The organic layer was separated, washed with 1N HCl and water, dried over MgSO4 and evaporated in vacuo to give 3-(3-chlorophenyl)-3-methylbutan-2-one (3.9 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.29 (m, 3H), 7.13 (m, 1H), 1.97 (s, 3H), 1.47 (s, 6H).

후처리

  1. stirringAfter stirring 1 h
  2. customThe reaction mixture was partitioned in CH2Cl2
  3. customThe organic layer was separated
  4. washwashed with 1N HCl and water
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-c40bc163500247ef901d272f08df84a8
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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