Tetrabutylammonium Fluoride → (S)-ethyl 2-tert-butoxy-2-(6-chloro-1-hydroxy-3-methylnaphthalen-2-yl)acetate

HRID 926146Notes

Reaction equation

HRID 926146 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:23])[CH:18]=2)[C:13]=1[O:24]S(C(F)(F)F)(=O)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:23])[CH:18]=2)[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89681783(S)-ethyl 2-tert-butoxy-2-(6-chloro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

Product 1

HCID 89681780(S)-ethyl 2-tert-butoxy-2-(6-chloro-1-hydroxy-3-methylnaphthalen-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(6-chloro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate (1.521 g, 3.15 mmol) in anhydrous THF (30 mL) at 0° C. was added a 1M solution of tetrabutylammonium fluoride in THF (6.30 mL. 6.30 mmol) to give a bright yellow solution. The reaction mixture was stirred for 45 minutes and quenched with saturated ammonium chloride solution and stirred for 5 minutes. The product was extracted with ethyl acetate/hexane (1:1, 2×). The combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C19H24ClO4: 349.1. Found: 349.1.

Workup

  1. customto give a bright yellow solution
  2. customquenched with saturated ammonium chloride solution
  3. stirringstirred for 5 minutes
  4. extractionThe product was extracted with ethyl acetate/hexane (1:1, 2×)
  5. dry with materialThe combined organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d5b8f0f7a6564c27ba611aa8a586886e
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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