Acetic acid, bromo-, diphenylmethyl ester → HCID 13603078, compound

HRID 2231980Notes

Reaction equation

HRID 2231980 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:15][C:16]([O:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1>[C:20]1([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:18][C:16]([CH2:15][N:5]2[CH:6]=[CH:7][C:2](=[O:1])[CH:3]=[CH:4]2)=[O:17])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11130534Acetic acid, bromo-, diphenylmethyl esterHCID 23665647Potassium tert-butoxideHCID 178418642HCID 178418642, compound

Product 1

HCID 13603078HCID 13603078, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.37 g of 4-hydroxypyridine was dissolved in 16 ml of THF, then 1.63 g of potassium tert-butoxide was added and reacted overnight. Thereafter, 3.12 g of diphenylmethyl bromoacetate was added and reacted for 6 hours. After the reaction, the solvent was removed, the residue was dissolved in chloroform and washed with water. This was dried over magnesium sulfate, the solvent was removed, and the residue was purified on silica gel chromatography using chloroform-methanol (20:1) to obtain 2.25 g of the title compound (55%).

Workup

  1. customreacted overnight
  2. customreacted for 6 hours
  3. customAfter the reaction
  4. customthe solvent was removed
  5. dissolutionthe residue was dissolved in chloroform
  6. washwashed with water
  7. dry with materialThis was dried over magnesium sulfate
  8. customthe solvent was removed
  9. customthe residue was purified on silica gel chromatography

Sources & evidence

ORD record
ord-8e8671beed454ee6a77e2b198e0281da
Source dataset
uspto-grants-1988_11
Patent number
US04785090

Reaction notes

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