Sodium Thiosulfate → HCID 62800456, compound

HRID 2076072Notes

Reaction equation

HRID 2076072 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[OH:16].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:16]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 62791926HCID 62791926, compound

Product 1

HCID 62800456HCID 62800456, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-(2,5-dichloro-phenyl)-cycloheptanol (0.6 g, 2.32 mmol) in dichloromethane (40 mL) was added Dess-Martin perjodane (1.22 g, 2.78 mmol). The mixture was stirred at 20° C. for 1 h. A mixture of 10% aq sodium bicarbonate solution (10 mL) and 10% aq sodium thiosulfate solution (10 mL) was added, and stirring was continued for 5 min. The organic layer was separated and dried over sodium sulfate. Solvents were removed under reduced pressure and the remaining oil was purified by column chromatography on silica gel using heptane/0-20% ethyl acetate as eluent to give the title compound (0.58 g, ca. 100%) as a pale-yellow oil. MS ISP (m/e): 257.1 [(M+H)+].

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 5 min
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customSolvents were removed under reduced pressure
  7. customthe remaining oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f83de52fdcc9402a919811a4e79646ec
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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