Water → HCID 21998069, compound

HRID 1977447Notes

Reaction equation

HRID 1977447 reaction equation
[Si]([O:8][C:9]1[CH:47]=[CH:46][C:12]([O:13][C:14]([C:16]2[CH:17]=[C:18]([N:39]3[C:43](=[O:44])[CH:42]=[CH:41][C:40]3=[O:45])[CH:19]=[C:20]([C:22]([O:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][Si](C(C)(C)C)(C)C)=[CH:27][CH:26]=3)=[O:23])[CH:21]=2)=[O:15])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.F.[F-].[Na+].O>C1COCC1>[OH:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][C:22]([C:20]2[CH:19]=[C:18]([N:39]3[C:43](=[O:44])[CH:42]=[CH:41][C:40]3=[O:45])[CH:17]=[C:16]([C:14]([O:13][C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:47][CH:46]=3)=[O:15])[CH:21]=2)=[O:23])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 14917Hydrofluoric AcidHCID 21998068HCID 21998068, compound

Product 1

HCID 21998069HCID 21998069, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[3,5-di-(4-(tert-butyldimethylsilyloxy)phenoxycarbonyl)phenyl]maleimide (35 g 0.052 mole) was dissolved in THF (500 ml). Hydrogen fluoride (2.5 M, 70 ml), sodium fluoride (3 g) and water (280 ml) were added. The reaction mixture was stirred overnight and most of the solvent was removed. Filtration of the product over a silica bed and concentration in vacuo afforded N-[3,5-di-(4-hydroxyphenoxycarbonyl)phenyl]maleimide (22.2 g, 96%).

Workup

  1. customwas removed
  2. filtrationFiltration of the product
  3. concentrationover a silica bed and concentration in vacuo

Sources & evidence

ORD record
ord-0523a097ce0e440fb0bacd741529896d
Source dataset
uspto-grants-2001_05
Patent number
US06232430B1

Reaction notes

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