Tetrahydrofuran → 3,7,11-Trimethyl-12-(methoxymethyl)oxy-6,10-dodecadien-1-in-3-ol

HRID 5659Notes

Reaction equation

HRID 5659 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:18])[CH2:13][O:14][CH2:15][O:16][CH3:17])=[CH:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].[Cl-].[NH4+].O1CC[CH2:23][CH2:22]1>>[CH3:7][C:6]([OH:8])([CH2:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:18])[CH2:13][O:14][CH2:15][O:16][CH3:17])[C:22]#[CH:23]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 540769986,10-Dimethyl-11-(methoxymethyl)oxy-5,9-undecadien-2-one

Product 1

HCID 1317181583,7,11-Trimethyl-12-(methoxymethyl)oxy-6,10-dodecadien-1-in-3-olYield 83%

Procedure

A solution of 6,10-dimethyl-11-(methoxymethyl)oxy-5,9-undecadien-2-one (67 mg, 0.26 mmol) in tetrahydrofuran (2 ml) was stirred on an ice bath under argon atmosphere. To the solution was added lithium acetylide ethylenediamine complex (30 mg, 0.33 mmol), and the mixture was warmed to room temperature and stirred for 3 hours. After addition of saturated aqueous ammonium chloride (2 ml), the reaction mixture was extracted with ether. The extract was dried over Na2SO4 and evaporated in vacuo to remove the solvent to give a crude product, which was purified with silica gel column chromatography to obtain 3,7,11-trimethyl-12-(methoxymethyl)oxy-6,10-dodecadien-1-in- 3-ol (61 mg, 83%).

Workup

  1. additionTo the solution was added lithium acetylide ethylenediamine complex (30 mg, 0.33 mmol)
  2. extractionthe reaction mixture was extracted with ether
  3. dry with materialThe extract was dried over Na2SO4
  4. customevaporated in vacuo
  5. customto remove the solvent
  6. customto give a crude product, which
  7. customwas purified with silica gel column chromatography

Sources & evidence

ORD record
ord-fb88b86a266648a883be899ba27a392c
Source dataset
uspto-grants-1993_09
Patent number
US05245085

Reaction notes

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