Tetrahydrofuran → 3,7,11-Trimethyl-12-(2-tetrahydropyranyl)oxy-6,10-dodecadien-1-in-3-ol

HRID 5658Notes

Reaction equation

HRID 5658 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:21])[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)=[CH:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].[Cl-].[NH4+].O1CC[CH2:26][CH2:25]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]([CH3:21])[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[C:25]#[CH:26]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 539858946,10-Dimethyl-11-(2-tetrahydropyranyl)oxy-5,9-undecadien-2-one

Product 1

HCID 1317181573,7,11-Trimethyl-12-(2-tetrahydropyranyl)oxy-6,10-dodecadien-1-in-3-olYield 75%

Procedure

A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (90 mg, 0.31 mmol) in tetrahydrofuran (5 ml) was stirred on an ice bath under argon atmosphere. To the solution was added lithium acetylide ethylenediamine complex (180 mg, 1.95 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-(2-tetrahydropyranyl)oxy-6,10-dodecadien-1-in-3-ol (75 mg, 75%).

Workup

  1. additionTo the solution was added lithium acetylide ethylenediamine complex (180 mg, 1.95 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-def7012a35b24ca7acecda3599d33a87
Source dataset
uspto-grants-1993_09
Patent number
US05245085

Reaction notes

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