Dimethylformamide → HCID 53912487, compound

HRID 1781545Notes

Reaction equation

HRID 1781545 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH2:10]/[CH:11]=[C:12](/[CH2:14][CH2:15][C:16](O)=[O:17])\[CH3:13])[C:5]([OH:19])=[C:4]2[C:20]([O:22][CH2:23][C:3]=12)=[O:21].CN(C)C=O.S(Cl)([Cl:31])=O>ClCCl>[OH:19][C:5]1[C:6]([CH2:10][CH:11]=[C:12]([CH3:13])[CH2:14][CH2:15][C:16]([Cl:31])=[O:17])=[C:7]([O:8][CH3:9])[C:2]([CH3:1])=[C:3]2[C:4]=1[C:20](=[O:21])[O:22][CH2:23]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 446541Mycophenolic Acid

Product 1

HCID 53912487HCID 53912487, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of mycophenolic acid (320 g, 1 mol) and dimethylformamide (0.1 g) in dichloromethane (3.2L) at reflux was treated dropwise with thionyl chloride (82 mL, 1.12 mol). After one hour additional heating at reflux, the volatiles were distilled at reduced pressure leaving a gray solid residue of (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl -3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoyl chloride which was cooled and dissolved in anhydrous tetrahydrofuran (1L).

Workup

  1. temperatureAfter one hour additional heating
  2. temperatureat reflux
  3. distillationthe volatiles were distilled at reduced pressure

Sources & evidence

ORD record
ord-d4d6d955703f412fbc9575b9b91423d7
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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