Water → 3-Hydroxy-4-(hydroxymethyl)benzamide

HRID 355518Notes

Reaction equation

HRID 355518 reaction equation
[O:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[CH2:18]Br)[C:12]([NH2:14])=[O:13])[Si](C(C)(C)C)(C)C.[OH2:20]>CC#N.[F-].[K+]>[OH:1][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[CH2:18][OH:20])[C:12]([NH2:14])=[O:13]

Participants

5

Reactant 2

HCID 962WaterHCID 18942783HCID 18942783, compound2×

Product 1

HCID 189427893-Hydroxy-4-(hydroxymethyl)benzamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 522689Potassium FluorideSolvent

Procedure

To the solution of 3-t-butyldimethylsiloxy-4-bromomethylbenzamide (Compound 7.2) (0.101 g, 0.293, mmol) in 8 mL CH3CN, KF.2H2O (0.041 g, 0.44 mmol) in 4 mL H2O was added dropwise. The mixture was then stirred at room temperature for half hour. After the solvent was removed, the residue was absorbed on 500 mg silica gel. The product was obtained by flash chromatography (ethyl acetate:ethyl alcohol=10:1, Rf=0.8) as a white solid (0.0439 g, y==90.7%). 1H NMR (CD3CN) δ4.68(s,2H), 5.95(b,1H), 6.69(b,1H), 7.23-7.26(m,3H), 7.77(b,1H); 13C NMR (CD3Cl) δ60.66, 115.13, 119.44, 128.69, 133.07, 134.94, 156.10, 203.64.

Workup

  1. customAfter the solvent was removed
  2. customthe residue was absorbed on 500 mg silica gel
  3. customThe product was obtained by flash chromatography (ethyl acetate:ethyl alcohol=10:1, Rf=0.8) as a white solid (0.0439 g, y==90.7%)

Sources & evidence

ORD record
ord-5cd99808902c46d4bf18841df0dfe3b1
Source dataset
uspto-grants-1998_11
Patent number
US05831073

Reaction notes

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