Sodium Thiosulfate → HCID 86691578, compound

HRID 926206Notes

Reaction equation

HRID 926206 reaction equation
[OH:1][CH:2]([C:8]1[C:17]([CH3:18])=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]=1[O:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])[C:3]([O:5][CH2:6][CH3:7])=[O:4].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>[CH3:18][C:17]1[C:8]([C:2](=[O:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:9]([O:19][S:20]([C:23]([F:24])([F:25])[F:26])(=[O:22])=[O:21])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86691576HCID 86691576, compound

Product 1

HCID 86691578HCID 86691578, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-hydroxy-2-(3-methyl-1-(trifluoromethylsulfonyloxy) naphthalen-2-yl)acetate (5.5 g, crude) in DCM (160 mL) was treated with Dess-Martin periodinane (7.18 g, 16.9 mmol) at 23° C. After 1 h, the reaction was added slowly over 5 min to 10% Na2S2O3 (100 mL). After 30 min, the reaction was extracted with DCM (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was treated with benzene, filtered, and loaded onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product in semi pure form. 1H NMR (400 MHz, CDCl3): δ 8.11-8.08 (m, 1H), 7.86-7.83 (m, 1H), 7.76 (s, 1H), 7.66-7.60 (m, 2H), 4.41 (q, J=7.4 Hz, 2H), 2.50 (s, 3H), 1.40 (t, J=7.4 Hz, 3H). 19F NMR (377 MHz, CDCl3) δ −73.3 (s).

Workup

  1. waitAfter 30 min
  2. extractionthe reaction was extracted with DCM (3×50 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe residue was treated with benzene
  7. filtrationfiltered
  8. custompurified by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b113b6607818402b844ebb26d9eba21c
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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