Trifluoromethanesulfonic anhydride → 5-Methoxynaphthalen-1-yl trifluoromethanesulfonate

HRID 1470486노트

반응식

HRID 1470486 반응식
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[OH:13].CCN(C(C)C)C(C)C.[O:23](S(C(F)(F)F)(=O)=O)[S:24]([C:27]([F:30])([F:29])[F:28])(=O)=[O:25]>ClCCl>[F:28][C:27]([F:30])([F:29])[S:24]([O:13][C:8]1[C:9]2[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:25])=[O:23]

참가 물질

5

반응물 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 110629015-Methoxynaphthalen-1-ol

생성물 1

HCID 110667265-Methoxynaphthalen-1-yl trifluoromethanesulfonate수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-methoxynaphthalen-1-ol (above Step-1 intermediate) (19 g, 0.11 mol) in anhydrous dichloromethane (250 mL) at 0° C. was added, DIPEA (23 mL, 0.16 mol) and the mixture was stirred for 15 min. To this, Tf2O (21.7 mL, 0.13 mol) was added slowly at 0° C. and the reaction mixture was stirred for 1.5 h and then quenched slowly with water (100 mL). The aqueous layer was extracted with CH2Cl2 (4×100 mL) and the combined organic layer was washed with water (100 mL), brine (100 mL), dried and filtered. The solvent was then evaporated and the crude product was purified by column chromatography (5% EtOAc:Hexanes) to furnish the desired compound (28.5 g, 85%) as a white solid.

후처리

  1. customquenched slowly with water (100 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (4×100 mL)
  3. washthe combined organic layer was washed with water (100 mL), brine (100 mL)
  4. customdried
  5. filtrationfiltered
  6. customThe solvent was then evaporated
  7. customthe crude product was purified by column chromatography (5% EtOAc:Hexanes)

출처 및 근거

ORD 기록
ord-fdc2a85c234a4414989996076cc1a015
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006442B2

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