Acetic Anhydride → 1-Triphenylmethyl-3,5-diacetoxymethylpyrazole

HRID 262345Notes

Reaction equation

HRID 262345 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[C:12]([CH2:13][OH:14])=[CH:11][C:10]([CH2:15][OH:16])=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30].[OH-:36].[Na+].CCN([CH2:43][CH3:44])CC>>[C:23]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:8]2[C:12]([CH2:13][O:14][C:29](=[O:31])[CH3:30])=[CH:11][C:10]([CH2:15][O:16][C:43](=[O:36])[CH3:44])=[N:9]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 123775321-Trityl-3,5-bis(hydroxymethyl)pyrazole

Product 1

HCID 123775331-Triphenylmethyl-3,5-diacetoxymethylpyrazole

Procedure

A solution of 19.5 g. (0.053 mol) of the end product of Example 19, 90 ml. of acetic anhydride and 20 ml. of Et3N was stirred at room temperature for 2.5 hours. After pouring into 1N NaOH, the solution was extracted with CH2Cl2. The organic phase was dried (MgSO4), concentrated and the residue recrystallized from CH3OH to give the end product. The analytical sample was prepared from the same solvent; colorless plates; mp 119°-121°.

Workup

  1. extractionthe solution was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customthe residue recrystallized from CH3OH
  5. customto give the end product
  6. customThe analytical sample was prepared from the same solvent

Sources & evidence

ORD record
ord-f8ae79ce1b384cc2a27e666ee61f4003
Source dataset
uspto-grants-1979_05
Patent number
US04153799

Reaction notes

Loading…