Acetic Anhydride → HCID 14307642, compound

HRID 2292067Notes

Reaction equation

HRID 2292067 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][C:8]2[O:9][C:10]3[C:17](=[O:18])[C:16]([CH3:19])=[C:15]([CH3:20])[C:14](=[O:21])[C:11]=3[C:12]=2[CH3:13])=[CH:5][CH:4]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH3:32][C:33](OC(C)=O)=[O:34].[CH3:39][CH2:40][O:41]C(C)=O>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:33]([O:21][C:14]1[C:11]2[C:12]([CH3:13])=[C:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=3)[O:9][C:10]=2[C:17]([O:18][C:40](=[O:41])[CH3:39])=[C:16]([CH3:19])[C:15]=1[CH3:20])(=[O:34])[CH3:32]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 14257810HCID 14257810, compound

Product 1

HCID 14307642HCID 14307642, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 2-(4-methoxybenzyl)-3,5,6-trimethyl-4,7-benzofurandione (from Preparation 3) (0.5 g) in EtOAc (50 mL) was stirred vigorously with a saturated aqueous solution of Na2S2O4 (50 mL) at 25° C. for 16 h. The organic layer was separated, dried (MgSO4) and the solvent evaporated to give a white solid. The solid was dissolved in pyridine (10 mL) containing at catalytic amount of 4-(dimethylamino)pyridine and 3 equivalents of Ac2O were added.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. customthe solvent evaporated
  4. customto give a white solid
  5. additionwere added

Sources & evidence

ORD record
ord-eb5d2dec6b23443e86535c113e2f8d28
Source dataset
uspto-grants-1989_01
Patent number
US04800228

Reaction notes

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