Sodium Thiosulfate → HCID 68107961, compound

HRID 2364726Notes

Reaction equation

HRID 2364726 reaction equation
[CH2:1]([C:4]1[C:19]([OH:20])=[C:18]([N+:21]([O-:23])=[O:22])[CH:17]=[CH:16][C:5]=1[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:32])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCCl>[OH:32][CH2:3][CH:2]1[CH2:1][C:4]2=[C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[C:19]2[O:20]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 68107442HCID 68107442, compound

Product 1

HCID 68107961HCID 68107961, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

Benzyl 2-allyl-3-hydroxy-4-nitro-benzoate 29c (1.36 g, 4.30 mmol) was dissolved in 100 mL of 1,2-dichloroethane followed by the addition of m-chloroperbenzoic acid (1.18 g, 4.77 mmol). The reaction solution was heated to 70° C. and stirred for 3 hours. The resulting solution was cooled down to room temperature, added with 20 mL of saturated sodium thiosulfate solution, stirred for 30 minutes and extracted with ethyl acetate (20 mL×3). The combined organic phase was washed with water (20 mL), saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound benzyl 2-(hydroxymethyl)-7-nitro-2,3-dihydrobenzofuran-4-carboxylate 29d (430 mg, yield: 30.1%) as a light yellow solid.

Workup

  1. temperatureThe resulting solution was cooled down to room temperature
  2. stirringstirred for 30 minutes
  3. extractionextracted with ethyl acetate (20 mL×3)
  4. washThe combined organic phase was washed with water (20 mL), saturated sodium chloride solution (20 mL) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1c4e72f9c55042b6ac08a59f0cc1ea92
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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