Triphenylphosphine → 3-Ethyl-5-methyl-1-benzoyloxy-4-(4-(3-methyl-2-butenyloxy)butyloxy)benzene

HRID 369685Notes

Reaction equation

HRID 369685 reaction equation
[CH3:1][C:2]([CH3:11])=[CH:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[CH2:12]([C:14]1[CH:19]=[C:18]([O:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=[C:16]([CH3:29])[C:15]=1O)[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:12]([C:14]1[CH:19]=[C:18]([O:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=[C:16]([CH3:29])[C:15]=1[O:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][CH:3]=[C:2]([CH3:11])[CH3:1])[CH3:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 232823894-[(3-Methylbut-2-en-1-yl)oxy]butan-1-olHCID 232824092-Ethyl-6-methyl-4-benzoyloxyphenol

Product 1

HCID 232824103-Ethyl-5-methyl-1-benzoyloxy-4-(4-(3-methyl-2-butenyloxy)butyloxy)benzeneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.52 g of 4-(3-methyl-2-butenyloxy)butanol, 0.77 g of 2-ethyl-6-methyl-4-benzoyloxyphenol, 0.87 g of triphenylphosphine and 20 ml of tetrahydrofuran was slowly added dropwise 0.73 g of diisopropyl 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 0.94 g of 3-ethyl-5-methyl-1-benzoyloxy-4-(4-(3-methyl-2-butenyloxy)butyloxy)benzene (yield, 79%), nD20.0 1.5361.

Workup

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

Sources & evidence

ORD record
ord-9d5aacd313c64550bdb3121819980b13
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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