Trifluoromethanesulfonic anhydride → 5-Methoxynaphthalen-1-yl trifluoromethanesulfonate

HRID 1470486Notes

Reaction equation

HRID 1470486 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 110667265-Methoxynaphthalen-1-yl trifluoromethanesulfonateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fdc2a85c234a4414989996076cc1a015
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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