Sodium Thiosulfate → Ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

HRID 926171Notes

Reaction equation

HRID 926171 reaction equation
[CH3:1][C:2]1[C:3]([CH: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.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.C(O)(C)C>[CH3:1][C:2]1[C:3]([C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:4]([O:13][S:14]([C:17]([F:18])([F:19])[F:20])(=[O:16])=[O:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 89676528Ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

Product 1

HCID 89676478Ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate (˜22.8 g, 56 mmol) in DCM (560 mL) was treated with solid Dess-Martin periodinane (35.7 g, 84.2 mmol) at room temperature. After 60 minutes, isopropyl alcohol (25 mL) was added and allowed to stir for 30 minutes. A mixture of saturated NaHCO3 and saturated Na2S2O3 (100 mL each, diluted to 400 mL with water) was added and the resulting aqueous layer extracted with DCM. The combined organics were washed with water, brine and dried over anhydrous MgSO4 and filtered. Following concentration in vacuo, the residue was purified via Isco silica gel column chromatography (0-35% EtOAc/hex) to afford ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate. 1H-NMR: 400 MHz, (CDCl3) δ: 7.98 (d, J=8.4 Hz, 1H); 7.66 (s, 1H); 7.61 (s, 1H); 7.47 (d, J=8.4 Hz, 1H); 4.41 (q, J=7.2 Hz, 2H); 2.55 (s, 3H); 2.49 (s, 3H); 1.40 (t, J=8.4 Hz, 3H).

Workup

  1. additionwas added
  2. extractionthe resulting aqueous layer extracted with DCM
  3. washThe combined organics were washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentration in vacuo
  7. customthe residue was purified via Isco silica gel column chromatography (0-35% EtOAc/hex)

Sources & evidence

ORD record
ord-dd668199040746a78613e338757706ac
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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