Triethylamine → Pentadecalactone

HRID 2419218Notes

Reaction equation

HRID 2419218 reaction equation
[I-].ClC1C=CC=C[N+]=1C.O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26].C(N(CC)CC)C>C(#N)C>[CH2:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:26])[O:27][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7836015-Hydroxypentadecanoic acidHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 235414PentadecalactoneYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a refluxing solution of 510 mg (2.0 mmol) of 2-chloro-1-methylpyridinium iodide in 50 ml of acetonitrile, there was added a solution of 134 mg (0.5 mmol) of 15-hydroxypentadecanoic acid and 404 mg (4.0 mmol) of triethylamine in 40 ml of acetonitrile over a period of 8 hours at a continuous and uniform rate, and the reaction mixture was refluxed for an additional 30 minutes after the addition was completed. After evaporation of the solvent, the residue was separated chromatographically on a silica gel column. 1,15-pentadecanolide was obtained in 84% yield.

Workup

  1. temperaturethe reaction mixture was refluxed for an additional 30 minutes
  2. additionafter the addition
  3. customAfter evaporation of the solvent
  4. customthe residue was separated chromatographically on a silica gel column

Sources & evidence

ORD record
ord-d8b4ebd69c2b463ab7fdd71f2d2a3ef8
Source dataset
uspto-grants-1978_08
Patent number
US04105673

Reaction notes

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