p-Toluenesulfonic acid monohydrate → tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one

HRID 2106841Notes

Reaction equation

HRID 2106841 reaction equation
[CH2:1]([C@H:7]([CH:11]([OH:32])[CH2:12][CH:13](OC1CCCCO1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:8](O)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH2:33].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([C@@H:7]1[CH:11]([OH:32])[CH2:12][CH:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:33][C:8]1=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 678557542-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid

Product 1

HCID 67855756tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(M)(a) 15.4 g of a diastereomer mixture of 2-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid were dissolved in 160 ml of ethanol and 800 mg of toluene-4-sulfonic acid monohydrate were added. The reaction mixture was heated to 55°-60° C. until the reaction was finished. The solvent was removed in vacuo and the residue was dissolved in 160 ml of dichloromethane. The solution was stirred at room temperature for 1 hour. The reaction mixture was evaporated. The material obtained was chromatographed on silica gel. There was obtained tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one, m.p. 95°-96° C.

Workup

  1. temperatureThe reaction mixture was heated to 55°-60° C. until the reaction
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 160 ml of dichloromethane
  4. customThe reaction mixture was evaporated
  5. customThe material obtained
  6. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-008104a8bc774009bd6d62250f68105f
Source dataset
uspto-grants-1990_06
Patent number
US04931463

Reaction notes

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