Ethyl orthoformate → HCID 67518179, compound

HRID 2173350Notes

Reaction equation

HRID 2173350 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][O:8][C:4]=2[CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+].[CH:19](OCC)(OCC)OCC>C(O)(=O)C>[N:1]1([C:2]2[CH:14]=[CH:13][C:5]3[CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][O:8][C:4]=3[CH:3]=2)[CH:19]=[N:17][N:16]=[N:15]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 67516008HCID 67516008, compound

Product 1

HCID 67518179HCID 67518179, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of methyl 6-amino-2,3-dihydro-1-benzofuran-3-carboxylate (2.51 g, 13 mmol), sodium azide (1.01 g, 15.6 mmol) and triethyl orthoformate (5.92 g, 40 mmol) in 30 mL of acetic acid was heated to 100° C. for 3 hrs. After the reaction was completed, the mixture was cooled to ambient temperature and the solvent was removed under vacuum. The residue was diluted with EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified with silica gel column chromatograph to give the crude product, then re-crystalization from DCM to give methyl 6-(1H-tetrazol-1-yl)-2,3-dihydro-1-benzofuran-3-carboxylate.

Workup

  1. customthe solvent was removed under vacuum
  2. additionThe residue was diluted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatograph
  7. customto give the crude product
  8. customre-crystalization from DCM

Sources & evidence

ORD record
ord-d21b509ad81e4e42ba83ef6c695f10ad
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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