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

HRID 236728Notes

Reaction equation

HRID 236728 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 1 N 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-afd001a5b23040c2b9af7d90e6d92445
Source dataset
uspto-grants-1979_06
Patent number
US04157331

Reaction notes

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