Sodium Thiosulfate → HCID 86691571, compound

HRID 514160Notes

Reaction equation

HRID 514160 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[C:4]([CH:20]([OH:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:3]=1[CH3:27].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][S:13]([C:16]([F:19])([F:17])[F:18])(=[O:14])=[O:15])=[C:4]([C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:3]=1[CH3:27]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86691572HCID 86691572, compound

Product 1

HCID 86691571HCID 86691571, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-(4-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate (crude, 1.22 g, ˜2.60 mmol) in DCM (60 mL) was treated with Dess-Martin periodinane (1.32 g, 3.12 mmol) at 23° C. After 30 min, 10% Na2S2O3 (30 mL) was added at 23° C. The system was diluted with H2O (20 mL) and extracted with DCM (3×30 mL). Combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was treated with benzene, filtered, and wet-loaded onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product (1.18 g, 98% yield over 2 steps from ethyl 2-(4-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate). 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=8.6 Hz, 1H), 8.13 (d, J=8.2 Hz, 1H), 7.77 (dd, J=8.6, 8.2 Hz, 1H), 7.71 (dd, J=8.6, 8.6 Hz, 1H), 4.42 (q, J=7.0 Hz, 2H), 2.57 (s, 3H), 1.39 (t, J=7.0 Hz, 3H). 19F NMR (377 MHz, CDCl3) δ−73.3 (s).

Workup

  1. extractionextracted with DCM (3×30 mL)
  2. dry with materialCombined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe residue was treated with benzene
  6. filtrationfiltered
  7. customwet-loaded onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fe2e4d9d52a04f479d5a1e20e503ea1b
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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