Triethylamine → Pentadecalactone

HRID 2419221Notes

Reaction equation

HRID 2419221 reaction equation
F[B-](F)(F)F.ClC1C=CC=C[N+]=1CC.O[CH2:16][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][C:30]([OH:32])=[O:31].C(N(CC)CC)C>C(#N)C>[CH2:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:31])[O:32][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7836015-Hydroxypentadecanoic acidHCID 11770253HCID 11770253, compound

Product 1

HCID 235414PentadecalactoneYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a refluxing solution of 460 mg (2.0 mmol) of 2-chloro-1-ethylpyridinium tetrafluoroborate 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 75% 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-c501168d23f14a25b8aa549f2bb9074f
Source dataset
uspto-grants-1978_08
Patent number
US04105673

Reaction notes

Loading…