Perchloric Acid → (S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

HRID 926228Notes

Reaction equation

HRID 926228 reaction equation
[CH3:1][C:2]1[C:3]([C@H:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:4]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2.Cl(O)(=O)(=O)=O>C(OC(C)=O)(C)(C)C>[C:2]([O:27][C@@H:21]([C:3]1[C:2]([CH3:1])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:12])[CH:9]=2)[C:4]=1[O:13][S:14]([C:17]([F:19])([F:20])[F:18])(=[O:15])=[O:16])[C:22]([O:24][CH2:25][CH3:26])=[O:23])([CH3:3])([CH3:11])[CH3:1]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 89681758(S)-ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate

Product 1

HCID 89681723(S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

A solution of (S)-ethyl 2-(3,6-dimethyl-1-(trifluoromethyl-sulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate (7.5 g, 18.5 mmol) in tBuOAc (100 mL) at room temperature was treated with perchloric acid (70%, 0.16 mL, 1.8 mmol) and allowed to stir at room temperature overnight. The reaction was slowly poured into ice-cold saturated NaHCO3 (150 mL). The aqueous layer was extracted with EtOAc and the combined organics washed with brine and dried over anhydrous MgSO4 and filtered. Following concentration in vacuo, purification of the residue by Yamazen silica gel column chromatography (2-20-50% EtOAc/hex) afforded (S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate. LCMS-ESI+ (m/z): [M+Na]+ calcd for C21H25F3O6SNa: 485.5. found: 485.8.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe combined organics washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentration
  6. customin vacuo, purification of the residue by Yamazen silica gel column chromatography (2-20-50% EtOAc/hex)

Sources & evidence

ORD record
ord-70be9f5e74c54b76852eb5d2f244c78a
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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