Pyridine → 12-Methoxycarbonyloxy-15-pentadecanolide

HRID 1109256Notes

Reaction equation

HRID 1109256 reaction equation
[OH:1][CH:2]1[CH2:18][CH2:17][CH2:16][O:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.N1C=CC=CC=1.Cl[C:26]([O:28][CH3:29])=[O:27]>C(Cl)Cl>[CH3:29][O:28][C:26]([O:1][CH:2]1[CH2:18][CH2:17][CH2:16][O:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 309431913-Hydroxy-oxacyclohexadecan-2-one

Product 1

HCID 1504169112-Methoxycarbonyloxy-15-pentadecanolideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

480 g (1.89 mol) of 12-hydroxy-15-pentadecanolide (VII) are dissolved in 900 ml of methylene chloride with 205.5 g of pyridine. 213 g (2.2 mol) of methyl chloroformate in 900 ml of methylene chloride are added dropwise to this mixture at 0° to 5° C. in the course of 1 hour. The reaction mixture is stirred at room temperature for a further 5 hours. The organic phase is washed neutral and dried over Na sulphate. The organic phase is freed from methylene chloride and subjected to fractional distillation. 540 g of 12-methoxycarbonyloxy-15-pentadecanolide are obtained; yield: 91% of theory.

Workup

  1. washThe organic phase is washed neutral
  2. dry with materialdried over Na sulphate
  3. distillationsubjected to fractional distillation

Sources & evidence

ORD record
ord-edc970c7baa3487f8f58f80e7ceb9e45
Source dataset
uspto-grants-1994_06
Patent number
US05319104

Reaction notes

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