Diethyl Ether → (2S,5S)-2-(4'-octyloxycarbonylbenzyloxy)-5-hexyl-delta-valerolactone

HRID 893253Notes

Reaction equation

HRID 893253 reaction equation
Br[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:8])=[CH:5][CH:4]=1.[OH:20][C@H:21]1[CH2:27][CH2:26][C@@H:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:24][C:22]1=[O:23].C(OCC)C>CN(C)C=O.[Ag]=O>[CH2:10]([O:9][C:7]([C:6]1[CH:18]=[CH:19][C:3]([CH2:2][O:20][C@H:21]2[CH2:27][CH2:26][C@H:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:24][C:22]2=[O:23])=[CH:4][CH:5]=1)=[O:8])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14645393(2S,5R)-hydroxy-5-hexyl-delta-valerolactoneHCID 19891718Octyl p-bromomethylbenzoate

Product 1

HCID 22844672(2S,5S)-2-(4'-octyloxycarbonylbenzyloxy)-5-hexyl-delta-valerolactoneYield 2.2%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

In 1.5 ml of dry dimethylformamide were dissolved 180 mg of octyl p-bromomethylbenzoate and 100 mg of (2S,5R)-2-hydroxy-5-hexyl-δ-valerolactone, and 300 mg of silver oxide was added to the solution and the mixture was stirred overnight at room temperature to effect reaction. After the reaction, diethyl ether was added to the reacted solution to extract the reaction product. The extract was washed with a saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate. Diethyl ether was removed by distillation under a reduced pressure. The obtained crude product was purified by the silica gel column chromatography to obtain 5 mg of (2S,5S)-2-(4'-octyloxycarbonylbenzyloxy)-5-hexyl-δ-valerolactone.

Workup

  1. additionwas added to the solution
  2. customreaction
  3. additionwas added to the reacted solution
  4. extractionto extract the reaction product
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried on anhydrous magnesium sulfate
  7. customDiethyl ether was removed by distillation under a reduced pressure
  8. customThe obtained crude product
  9. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-b48a4ea2f39144efb591a471b81abbd8
Source dataset
uspto-grants-1992_06
Patent number
US05124069

Reaction notes

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