Triethylamine → Pentadecalactone

HRID 2419223Notes

Reaction equation

HRID 2419223 reaction equation
F[B-](F)(F)F.ClC1C(C)=CC=C[N+]=1CC.O[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32].C(N(CC)CC)C>C(#N)C>[CH2:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](=[O:32])[O:33][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7836015-Hydroxypentadecanoic acidHCID 20315191HCID 20315191, compound

Product 1

HCID 235414PentadecalactoneYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a refluxing solution of 486 mg (2.0 mmol) of 2-chloro-1-ethyl-3-methylpyridinium tetrafluoroborate in 50 ml of acetonitrile, there was added a solution of 129 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 78% 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-41933ca0a64d49868d9611b105e84f31
Source dataset
uspto-grants-1978_08
Patent number
US04105673

Reaction notes

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