Triethylamine → HCID 70489191, compound

HRID 638135Notes

Reaction equation

HRID 638135 reaction equation
O[CH:2]([CH3:15])[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11][C:12]([OH:14])=[O:13].C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C(#N)C>[C:12]1(=[O:14])[O:13][CH:2]([CH3:15])[CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH:9]=[CH:10][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 11063750HCID 11063750, compound

Product 1

HCID 70489191HCID 70489191, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of hydroxy-acid 14 (0.64 g, 3.1 mmol) and dry triethylamine (2.42 g, 24 mmol) in dry acetonitrile (200 mL) was added over 20 hr via a fixed-rate addition funnel and a high dilution head to a refluxing solution of 2-chloro-N-methyl-pyridinium iodide (3.18 g, 12.4 mmol) in dry acetonitrile (200 mL), under argon. The resulting solution was refluxed a further 2 hr, cooled, and concentrated in vacuo. The residue was taken up in pentane (50 mL) and washed with water (50 mL). The aqueous phase was extracted twice more with pentane (25 mL), and the combined pentane extracts were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was flash chromatographed (hexane:EtOAc, 40:1), yielding 45 mg (7.5% yield) of macrolide II. ##STR3##

Workup

  1. temperatureThe resulting solution was refluxed a further 2 hr
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. washwashed with water (50 mL)
  5. extractionThe aqueous phase was extracted twice more with pentane (25 mL)
  6. washthe combined pentane extracts were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customchromatographed (hexane:EtOAc, 40:1)

Sources & evidence

ORD record
ord-a72fff7e71be44c7b7668e4606067c17
Source dataset
uspto-grants-1985_12
Patent number
US04560551

Reaction notes

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