Ethanol → HCID 21693927, compound

HRID 703679Notes

Reaction equation

HRID 703679 reaction equation
[CH2:1]([CH:7]1[CH:10](CC(OC2CCCCO2)CCCCCCCCCCC)[O:9][C:8]1=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH+]1C=CC=CC=1.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41](S([O-])(=O)=O)=[CH:40][CH:39]=1.C([OH:51])C>>[OH:51][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:48][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:1][CH:7]1[CH2:10][O:9][C:8]1=[O:31]

Participants

4

Reactant 3

HCID 702EthanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 217639363-Hexyl-4-{2-[(oxan-2-yl)oxy]tridecyl}oxetan-2-one

Product 1

HCID 21693927HCID 21693927, compound

Procedure

(1B.a) 265 mg of an isomer mixture of 3-hexyl-4-[2-[(tetrahydro-2H-pyran-2-yl)oxy]tridecyl]-2-oxetanone are dissolved in 2.5 ml of ethanol and 13 mg of pyridinium-4-toluenesulphonate are added. The reaction mixture is heated to 55°-60° C. until the reaction has finished. The solvent is removed in vacuo and the residue is taken up in ether, whereby there separate crystals which are removed by filtration. The solvent is evaporated off in vacuo and the residue is chromatographed on silica gel. There is obtained rac-3-hexyl-4-(2-hydroxytridecyl-2-oxetanone (2R,3S,4S:2S, 3R,4R), MS: M+ (354), m.p. 44.5°-46° C.

Workup

  1. temperatureThe reaction mixture is heated to 55°-60° C. until the reaction
  2. customThe solvent is removed in vacuo
  3. customwhereby there separate crystals which
  4. customare removed by filtration
  5. customThe solvent is evaporated off in vacuo
  6. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-f7fc04616f0448c891486de42951599e
Source dataset
uspto-grants-1991_01
Patent number
US04983746

Reaction notes

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