Methanol → 5-(Diethoxymethyl)-3-methoxy-2-nitrothiophene

HRID 59753Notes

Reaction equation

HRID 59753 reaction equation
Br[C:2]1[CH:6]=[C:5]([CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[S:4][C:3]=1[N+:14]([O-:16])=[O:15].[CH3:17][OH:18].C[O-].[Na+]>>[CH2:9]([O:8][CH:7]([O:11][CH2:12][CH3:13])[C:5]1[S:4][C:3]([N+:14]([O-:16])=[O:15])=[C:2]([O:18][CH3:17])[CH:6]=1)[CH3:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 867038583-Bromo-5-(diethoxymethyl)-2-nitrothiophene

Product 1

HCID 867038595-(Diethoxymethyl)-3-methoxy-2-nitrothiopheneYield 403.1%

Conditions

Temperature
120 °C

Procedure

To a solution of 3-bromo-5-(diethoxymethyl)-2-nitrothiophene (Int. 66) (1 g, 3.22 mmol) in MeOH (10 ml) copper(II) oxide (0.051 g, 0.645 mmol), KI (10.7 mg, 0.064 mmol) and sodium methanolate (0.662 g, 12.25 mmol) were added, and the mixture was heated under MW irradiation at 120° C. for 2 hours. The reaction mixture was filtered through a celite pad, the filtrate was concentrated under vacuum and then partitioned between 0.5N HCl and EtOAc. The organic phase was dried over sodium sulfate, filtered and evaporated to give 5-(diethoxymethyl)-3-methoxy-2-nitrothiophene (Int. 67) (680 mg, 2.60 mmol, MS/ESI+261.0 [MH]+). This crude was used without any additional purification.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated under vacuum
  3. custompartitioned between 0.5N HCl and EtOAc
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-70e42477b2454f43bc0b4c6e243142dc
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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