Dimethylformamide → Dimethylmatairesinol

HRID 1753779Notes

Reaction equation

HRID 1753779 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]2[C@@H:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([O:24][CH3:25])[CH:23]=3)C(=O)O[CH2:12]2)[CH:6]=[CH:7][C:8]=1O.[C:27](=[O:30])([O-])[O-:28].[K+].[K+].I[CH3:34].CN([CH:38]=[O:39])C>>[CH3:38][O:39][C:8]1[CH:7]=[CH:6][C:5]([CH2:10][CH:11]2[CH:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:26][CH3:34])=[C:22]([O:24][CH3:25])[CH:23]=3)[C:27](=[O:30])[O:28][CH2:12]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 119205(-)-Matairesinol

Product 1

HCID 1286DimethylmatairesinolYield 90%

Procedure

Matairesinol (5 g, 13.95 mmol) was dissolved in DMF (20 ml) and potassium carbonate (9.64 g, 69.8 mmol), iodomethane (5.23 ml, 84 mmol) were added. The mixture was stirred at RT for 18 h and then DMF was partly evaporated under reduced pressure and mixture was diluted with water (50 ml). The formed insoluble oil was separated, dissolved in DCM, dried with Na2SO4 and evaporated to dryness to give 4.87 g, (90% yield) of dimethylmatairesinol as a yellowish powder.

Workup

  1. customDMF was partly evaporated under reduced pressure and mixture
  2. additionwas diluted with water (50 ml)
  3. customThe formed insoluble oil was separated
  4. dissolutiondissolved in DCM
  5. dry with materialdried with Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-518bd36527104695b849c8b1577d7268
Source dataset
uspto-grants-2015_10
Patent number
US09168243B2

Reaction notes

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