Methanesulfonyl chloride → Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester

HRID 1255058노트

반응식

HRID 1255058 반응식
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([OH:16])[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2].CCN(C(C)C)C(C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:16][S:28]([CH3:27])(=[O:30])=[O:29])[C:6]1[CH:7]=[CH:8][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:10][CH:11]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 20286794Hydroxy 4-(trifluoromethyl)phenylacetic acid ethyl ester

생성물 1

HCID 59401272Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester수율 100.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

Hydroxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester (I101) (440 mg, 1.77 mmol) and DIPEA (0.43 mL, 2.48 mmol) are dissolved in dry DCM (17 mL) and cooled at 0° C. under N2. Methansulfonyl chloride (0.18 mL, 2.30 mmol) is added dropwise to the solution and the resulting mixture is allowed to warm to RT and stirred for 3 hours. The mixture is diluted with DCM and washed with sat. NaHCO3, water and brine. The organic layer is dried (Na2SO4), filtered and evaporated to obtain intermediate I150 as a yellow oil (578 mg, quantitative yield), which is used in the next step without any further purification.

후처리

  1. temperatureto warm to RT
  2. washwashed with sat. NaHCO3, water and brine
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-cedbe4d6734f421b9961243269128141
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455646B2

반응 노트

불러오는 중…