Acetic Acid → HCID 58566476, compound

HRID 445849Notes

Reaction equation

HRID 445849 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.C(OCC)(OCC)OCC.[N-:28]=[N+:29]=[N-:30].[Na+].[C:32](O)(=O)C>O>[CH3:10][C:8]1([CH3:11])[CH2:7][C:6]2[CH:12]=[C:2]([N:1]3[CH:32]=[N:30][N:29]=[N:28]3)[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]=2[O:9]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 58566656HCID 58566656, compound

Product 1

HCID 58566476HCID 58566476, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 5-amino-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (675) (300 mg, 1.28 mmol), triethyl orthoformate (0.42 mL, 2.55 mmol), sodium azide (124.8 mg, 1.92 mmol), and acetic acid (12 mL) was heated at 100° C. for 2 hours. The reaction was cooled to room temperature and water was added. The aqueous phase was extracted with ethyl acetate and the combined organic layers dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (50%) to afford ethyl 2,2-dimethyl-5-(1H-tetrazol-1-yl)-2,3-dihydrobenzofuran-7-carboxylate (676) (184 mg, 50%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. dry with materialthe combined organic layers dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (50%)

Sources & evidence

ORD record
ord-6513415d24ed4940847c4f2f37d6c9f9
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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