Pyridine → HCID 70392119, compound

HRID 477438Notes

Reaction equation

HRID 477438 reaction equation
[CH2:1]([CH:17]1[CH2:21][CH:20]=[CH:19][O:18]1)[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].[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29].[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O>[Cl-:22].[CH2:1]([CH:17]1[CH2:21][CH2:20][CH:19]([O:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][N+:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:18]1)[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 1049Pyridine2×HCID 748286-Chloro-1-hexanolHCID 19835767HCID 19835767, compound

Product 1

HCID 70392119HCID 70392119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Analogous to Example 8 but (step a) using dimethylformamide as solvent starting from 2-hexadecyl-2,3-dihydrofuran and 6-chlorohexanol instead of 2-bromoethanol to give the trans and the cis 2-hexadecyl-5-(6'-chloro)-hexyloxy-tetrahydrofuran and (step b) performing the substitution of the chloro atom by pyridine by heating (60°-80° C.) 0.3 g (0.7 mmol) of each chloro compound, pyridine (2 ml) and dimethylformamide (2 ml) overnight with stirring. Evaporation of the excess of pyridine and dimethylformamide leaded to residus which were chromatographed on silica gel using successively 10, 15 and 20% MeOH in CHCl3 as eluents. The title compounds were recovered as waxy solids.

Workup

  1. customto give the trans
  2. customEvaporation of the excess of pyridine and dimethylformamide
  3. customwere chromatographed on silica gel using successively 10, 15 and 20% MeOH in CHCl3 as eluents
  4. customThe title compounds were recovered as waxy solids

Sources & evidence

ORD record
ord-a24fd053202d4728bcae9bdae46ee6c5
Source dataset
uspto-grants-1989_12
Patent number
US04888337

Reaction notes

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