Triphenylphosphine → 3,5-Diethyl-1-benzoyloxy-4-(4-(2,2-diethoxyethoxy)butyloxy)benzene

HRID 369686Notes

Reaction equation

HRID 369686 reaction equation
[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH3:2].[CH2:15]([C:17]1[CH:22]=[C:21]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[C:19]([CH2:32][CH3:33])[C:18]=1O)[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O-])=O)=NC([O-])=O>O1CCCC1>[CH2:15]([C:17]1[CH:22]=[C:21]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[C:19]([CH2:32][CH3:33])[C:18]=1[O:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:12][CH2:13][CH3:14])[CH3:16]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 184295442,6-Diethyl-4-benzoyloxyphenolHCID 184301114-(2,2-Diethoxyethoxy)butanolHCID 51573101N-carboxylatoiminocarbamate

Product 1

HCID 184296493,5-Diethyl-1-benzoyloxy-4-(4-(2,2-diethoxyethoxy)butyloxy)benzeneYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 16.0 g of 4-(2,2-diethoxyethoxy)butanol, 18.9 g of 2,6-diethyl-4-benzoyloxyphenol, 20.2 g of triphenylphosphine and 200 ml of tetrahydrofuran was slowly added dropwise 17.0 g of dilsopropyl azodicarboxylate with stirring under ice cooling. After stirring at room temperature for 6 hours, the reaction mixture was concentrated. The residue was subjected to silica gel chromatography, which afforded 31.4 g of 3,5-diethyl-1-benzoyloxy-4-(4-(2,2-diethoxyethoxy)butyloxy)benzene (yield, 88%), nD24.8 1.5129.

Workup

  1. stirringAfter stirring at room temperature for 6 hours
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-289d98d8811343da91d8e8279807d803
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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