Diethyl Ether → (E)-5-(2-nonyloxyphenyl)-3-hydroxy-3-methyl-1,4-pentadiene

HRID 1639214Notes

Reaction equation

HRID 1639214 reaction equation
[CH2:1]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]=[CH:18]C(=O)C)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH:22]([Mg]Br)=[CH2:23].[Cl-].[NH4+].[CH3:28][CH2:29]OCC.[O:33]1CCCC1>>[CH2:1]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[C:22]([OH:33])([CH3:23])[CH:28]=[CH2:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 540771084-(2-Nonyloxyphenyl)-3-butene-2-oneHCID 178418507HCID 178418507, compound

Product 1

HCID 14676402(E)-5-(2-nonyloxyphenyl)-3-hydroxy-3-methyl-1,4-pentadiene

Conditions

Temperature
0 °C

Procedure

A solution of 4-(2-nonyloxyphenyl)-3-butene-2-one (58 g) in tetrahydrofuran (200 mL) was added to a solution of vinylmagnesium bromide in tetrahydrofuran (200 mL, 1.6M diluted to lL with more tetrahydrofuran) at -30° C. After complete addition, the mixture was stirred at 0° C for 30 min qquenched with saturated aqueous ammonium chloride (100 mL) and ether (2L) and filtered free of solids. Concentration of the organic extract and purification by chromatography over siica gel yielded (E)-5-(2-nonyloxyphenyl)-3-hydroxy-3-methyl-1,4-pentadiene (40 g) as an oil.

Workup

  1. additionAfter complete addition
  2. filtrationfiltered free of solids
  3. extractionConcentration of the organic extract
  4. custompurification by chromatography over siica gel

Sources & evidence

ORD record
ord-50793ce83d7749f5bac3958569322cb3
Source dataset
uspto-grants-1989_11
Patent number
US04883614

Reaction notes

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