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Trifluoromethanesulfonyl chloride → Ethyl 4-methyl-2-(trifluoromethanesulfonyloxy)cyclohex-1-enecarboxylate

HRID 1383817
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HRID 1383817 반응식
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH:9]([CH3:13])[CH2:8][CH2:7]1)=[O:5].C(N(CC)C(C)C)(C)C.[F:23][C:24]([F:30])([F:29])[S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:13][CH:9]1[CH2:8][CH2:7][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[C:11]([O:12][S:25]([C:24]([F:30])([F:29])[F:23])(=[O:27])=[O:26])[CH2:10]1
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참가 물질

5

반응물 3

HCID 79000Trifluoromethanesulfonyl chloride2회HCID 81531Diisopropylethylamine2회HCID 98162Ethyl 4-methyl-2-oxocyclohexanecarboxylate

생성물 1

HCID 21187513Ethyl 4-methyl-2-(trifluoromethanesulfonyloxy)cyclohex-1-enecarboxylate수율 99.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of ethyl 4-methyl-2-cyclohexanone-1-carboxylate (50 g, 0.27 mol) in dichloromethane (500 ml) at −10° C. was added N,N-diisopropylethylamine (52 ml, 0.3 mol) followed by dropwise addition of trifluoromethanesulphonyl chloride (57 ml, 0.3 mol) keeping the temperature between −5 and −100° C. The reaction mixture was allowed to warm to room temperature and stirred for 3 hours. TLC showed 80% reaction, it was cooled to −5° C. and more N,N-diisopropylethylamine (14 ml, 0.1 mol) was added followed by trifluoromethanesulphonyl chloride (15.5 ml, 0.1 mol) and the reaction mixture was stirred for 15 hours at room temperature. The mixture was washed with cold water (2×200 ml), cold saturated sodium bicarbonate (2×200 ml) and brine (1×200 ml). The organic layer was dried (MgSO4), filtered and evaporated to give the required product (85 g) as a colourless oil. 1H NMR (250 MHz, CDCl3) δ 1.04 (3H, d, J=6.5 Hz), 1.43 (3H, m), 1.73-2.09 (4H, m), 2.39-2.63 (3H, m), 4.25 (2H, m).

후처리

  1. customthe temperature between −5 and −100° C
  2. custom80% reaction, it
  3. temperaturewas cooled to −5° C.
  4. stirringthe reaction mixture was stirred for 15 hours at room temperature
  5. washThe mixture was washed with cold water (2×200 ml), cold saturated sodium bicarbonate (2×200 ml) and brine (1×200 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-4074c702c7ca473097e8aa98fb7a7bcb
출처 데이터셋
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06255305B1

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