Triphenylphosphine → 4-((2,2-dimethoxy)ethyl)-1-((2E)-2-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenyloxy)benzene

HRID 128787

Reaction equation

HRID 128787 reaction equation
[CH3:1]/[C:2](=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]=1[CH3:18])/[CH2:3][OH:4].[CH3:19][O:20][CH:21]([O:30][CH3:31])[CH2:22][C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:31][O:30][CH:21]([O:20][CH3:19])[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:4][CH2:3]/[C:2](/[CH3:1])=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]=2[CH3:18])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19375035(2E)-2-Methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenolHCID 193750574-(2,2-Dimethoxyethyl)phenol

Product 1

HCID 193751194-((2,2-dimethoxy)ethyl)-1-((2E)-2-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenyloxy)benzeneYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2E)-2-Methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenol (1.5 g), 4-((2,2-dimethoxy)ethyl)phenol (1.1 g) and triphenylphosphine (1.59 g) are dissolved in THF (10 ml) and the solution cooled to 0°. Diethyl azodicarboxylate (1.05 ml, in 9 ml THF) is added dropwise with stirring, and the mixture is allowed to warm to room temperature and stirred overnight. The reaction mixture is concentrated and the residue is chromatographed with dichloromethane to provide 4-((2,2-dimethoxy)ethyl)-1-((2E)-2-methyl-7-(2,6,6-trimethyl- 1-cyclohexen-1-yl)-2-heptenyloxy)benzene as a pale yellow oil (2.27 g). This material is reacted with glyoxylic acid and morpholine hydrochloride by the method of Example 2 above, purified by chromatography with 7% ether in dichloromethane, and recrystallized from hexane-dichloromethane to provide the title compound as a white solid, mp 119°-121° (1.0 g).

Workup

  1. temperaturethe solution cooled to 0°
  2. stirringstirred overnight
  3. concentrationThe reaction mixture is concentrated
  4. customthe residue is chromatographed with dichloromethane

Sources & evidence

ORD record
ord-bddd97da5b604bebbb68997091d0006b
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Linked notes

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