Acetic Anhydride → HCID 67005800, compound

HRID 563427

Reaction equation

HRID 563427 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[OH:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.C(N=[N+]=[N-])C.[C:23](OC(=O)C)(=[O:25])[CH3:24]>C1COCC1>[C:23]([O:11][CH:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[CH:3]2)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 79118Ethane, azido-HCID 59252753HCID 59252753, compound

Product 1

HCID 67005800HCID 67005800, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1H-indazol-5-yl)(phenyl)methanol (1.1 g, 5.0 mmol) in 50 mL of dry THF was added EtN3 (2.8 mL, 20 mmol) and acetic anhydride (1.9 mL, 20 mmol). The reaction was heated at reflux for 12 h. The reaction was quenched with aqueous sodium bicarbonate and extracted 2×EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was taken up in toluene and concentrated in vacuo×2 to remove any excess acetic anhydride. Obtained a quantitative yield of (1H-indazol-5-yl)(phenyl)methyl acetate. MS found: (M+H)+=309.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 12 h
  3. customThe reaction was quenched with aqueous sodium bicarbonate
  4. extractionextracted 2×EtOAc
  5. dry with materialThe organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationconcentrated in vacuo×2
  9. customto remove any excess acetic anhydride

Sources & evidence

ORD record
ord-f191b46d9b794ff7b0905c440f0648a4
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Linked notes

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