Ammonium Chloride → 3,7,11-Trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-ol

HRID 1464464Notes

Reaction equation

HRID 1464464 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].[CH:22]([Mg]Br)=[CH2:23].[Cl-].[NH4+]>O1CCCC1>[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)[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 539858946,10-Dimethyl-11-(2-tetrahydropyranyl)oxy-5,9-undecadien-2-oneHCID 178418507HCID 178418507, compound

Product 1

HCID 678485313,7,11-Trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-olYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (80 mg, 0.27 mmol) in tetrahydrofuran (3 ml) was stirred on an ice bath under argon atmosphere. To the solution was added vinylmagnesium bromide in tetrahydrofuran (0.3 ml, 0.3 mmol, 1.0M), and the mixture was warmed to room temperature and stirred for 10 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-1,6,10-dodecatrien-3-ol (61 mg, 70%).

Workup

  1. extractionthe reaction mixture was extracted with ether
  2. dry with materialThe extract was dried over Na2SO4
  3. customevaporated in vacuo
  4. customto remove the solvent
  5. customto give a crude product, which
  6. customwas purified with silica gel column chromatography

Sources & evidence

ORD record
ord-3d47fb7c228f4897b41835c1f8154147
Source dataset
uspto-grants-1994_04
Patent number
US05304661

Reaction notes

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