Sodium Thiosulfate → Methyl 2-(hydroxymethyl)-7-nitro-2,3-dihydrobenzofuran-4-carboxylate

HRID 2364751Notes

Reaction equation

HRID 2364751 reaction equation
[CH2:1]([C:4]1[C:13]([OH:14])=[C:12]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:26])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[OH:26][CH2:3][CH:2]1[CH2:1][C:4]2=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[C:13]2[O:14]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59768300Methyl 2-allyl-3-hydroxy-4-nitro-benzoate

Product 1

HCID 68107371Methyl 2-(hydroxymethyl)-7-nitro-2,3-dihydrobenzofuran-4-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-allyl-3-hydroxy-4-nitro-benzoate 1d (0.47 g, 2 mmol) was dissolved in 80 mL of dichloromethane followed by the addition of m-chloroperbenzoic acid (0.99 g, 4 mmol). The reaction solution was stirred for 24 hours. The resulting solution was added with 20 mL of saturated sodium thiosulfate solution and 20 mL of saturated sodium bicarbonate solution successively, stirred for 5 minutes and extracted with ethyl acetate (20 mL×3). The combined organic phase was washed with water (20 mL) and 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 methyl 2-(hydroxymethyl)-7-nitro-2,3-dihydrobenzofuran-4-carboxylate 40a (440 mg, yield: 87.0%) as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-bff724e9edf5485d8d11e821ca063470
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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