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

HRID 1110171Notes

Reaction equation

HRID 1110171 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-f0ce53628e6a4df382e1c0868ffb6319
Source dataset
uspto-grants-1994_06
Patent number
US05324869

Reaction notes

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