Ammonium Chloride → HCID 70281429, compound

HRID 1456545Notes

Reaction equation

HRID 1456545 reaction equation
BrC1C=[C:4]2[CH:11]=[CH:10][C:9]([CH3:13])(C)[O:8][C:5]2=NC=1.[Li][CH2:15][CH2:16]CC.CN(C)[C:21](=[O:23])[CH3:22].[Cl-].[NH4+:26]>CCOCC>[C:21]([CH:5]1[O:8][C:9]2[CH:13]=[CH:15][CH:16]=[N:26][C:10]=2[CH:11]=[CH:4]1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 14117130HCID 14117130, compoundHCID 178418339Butyllithium

Product 1

HCID 70281429HCID 70281429, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-bromo-2,2-dimethyl-2H-pyrano[2,3-b]pyridine (1.2 g, prepared as in Synthetic Communs. 18, 1111 (1988)) in dry ether (30 ml) at -78° C. under Argon, was added dropwise a 2.5M solution of n-BuLi in hexanes (2 ml) over 5 min. followed by N,N-dimethylacetamide (0.55 ml). The resulting solution was stirred and allowed to attain room temperature. Saturated ammonium chloride solution (2 ml) was added to the solution. Extraction via ethyl acetate gave a crude solid (0.93 g) which was flash chromatographed on silica gel using ethyl acetate-hexane (3:7) as eluant to give acetylpyranopyridine (0.62 g) as a colourless solid.

Workup

  1. customto attain room temperature
  2. extractionExtraction via ethyl acetate
  3. customgave a crude solid (0.93 g) which
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-473248603809410dbe71dfd18fb3c7f9
Source dataset
uspto-grants-1998_12
Patent number
US05843989

Reaction notes

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