Water → 4-formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid methyl ester

HRID 1692625Notes

Reaction equation

HRID 1692625 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]([O:10][C:11]3[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[C:16]=3[O:17][C:6]=2[C:5]([CH:24]=[O:25])=[C:4]([OH:26])[CH:3]=1)=[O:9].[CH3:27]I.O>CN(C=O)C>[CH3:27][O:19][C:18]([C:15]1[C:16]2[O:17][C:6]3[C:5]([CH:24]=[O:25])=[C:4]([OH:26])[CH:3]=[C:2]([CH3:1])[C:7]=3[C:8](=[O:9])[O:10][C:11]=2[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=1)=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 23725Psoromic Acid

Product 1

HCID 148259704-formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Psoromic acid (1 mmol) was dissolved in DMF (10 mL), KHCO3 (2.4 mmol) was added and stirred for several minutes at room temperature. Then, CH3I (1.2 mmol) was added. The reaction mixture was maintained at 40° C. and monitored by TLC. Upon completion, the reaction mixture was poured into 50 mL of water and extracted with ethyl acetate. The organic layer was subsequently washed with saturated NaHCO3 solution and saturated brine, and dried over anhydrous MgSO4, filtered and evaporated by a rotatory evaporator. The residue was purified by column chromatography to provide a white solid product.

Workup

  1. temperatureThe reaction mixture was maintained at 40° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was subsequently washed with saturated NaHCO3 solution and saturated brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated by a rotatory evaporator
  7. customThe residue was purified by column chromatography
  8. customto provide a white solid product

Sources & evidence

ORD record
ord-9bb8f884ad5b4a54a0d30e43bbe4eaed
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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