Water → HCID 86082286, compound

HRID 645531Notes

Reaction equation

HRID 645531 reaction equation
Br[CH2:2][C:3]1[C:11]2[O:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[N-:12]=[N+:13]=[N-:14].[Na+].O>CN(C)C=O>[N:12]([CH2:2][C:3]1[C:11]2[O:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 685822037-(Bromomethyl)-2,3-dihydrobenzofuran

Product 1

HCID 86082286HCID 86082286, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 48B (4.40 g) in N,N-dimethylformamide (60 mL) at room temperature was treated in one portion with sodium azide (5.37 g), stirred for 3 hours, poured into water and extracted with diethylether (2×100 mL). The organics were dried (sodium sulfate), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (5% ethyl acetate/hexane) to provide the title compound. 1H NMR (CDCl3) δ 3.23 (t, 2H), 4.31 (s, 2H), 4.60 (t, 2H), 6.85 (t, 1H), 7.06 (d, 1H), 7.19 (dd, 1H).

Workup

  1. extractionextracted with diethylether (2×100 mL)
  2. dry with materialThe organics were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7f09984120e2484c8e2c9de7a6497f48
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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