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

HRID 2364751노트

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HRID 2364751 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bff724e9edf5485d8d11e821ca063470
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691822B2

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