Pyridine → HCID 23039593, compound

HRID 2166443Notes

Reaction equation

HRID 2166443 reaction equation
[CH2:1]([O:17][C:18]([O:20][CH2:21][C:22](=[CH2:32])[CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:33][S:34](Cl)(=[O:36])=[O:35].N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:17][C:18]([O:20][CH2:21][C:22](=[CH2:32])[CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][S:34]([CH3:33])(=[O:36])=[O:35])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 23039623HCID 23039623, compound

Product 1

HCID 23039593HCID 23039593, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Hexadecyloxycarbonyloxy-1-(6-hydroxyhexyloxy)-2-methylenepropane (from Preparation 51) (0.54 g) and methanesulfonyl chloride (0.20 g) were stirred in methylene chloride at 0° C. Pyridine (6 ml) was added and stirring continued for 15 minutes at 0° C. and for 2.5 hours at 22° C. Methylene chloride (10 ml) was added, and the organic phase was washed with water (3×15 ml), dried over magnesium sulfate, filtered and evaporated in vacuo to dryness. Purification was achieved by chromatography on silica gel 60 (70-230 mesh, 15 g) eluting with chloroform/ether/pentane 1:1:10 followed by chloroform/ether 1:1.

Workup

  1. washthe organic phase was washed with water (3×15 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo to dryness
  5. customPurification
  6. washeluting with chloroform/ether/pentane 1:1:10

Sources & evidence

ORD record
ord-5dd3d486bb514963aa9d50029ec10752
Source dataset
uspto-grants-1990_07
Patent number
US04945098

Reaction notes

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