2,5-Dichlorophenol → [3-(2,5-Dichlorophenoxy)pentyl]methylcarbamic acid, 1,1-dimethylethyl ester

HRID 2183834Notes

Reaction equation

HRID 2183834 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].O[CH:11]([CH2:23][CH3:24])[CH2:12][CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[CH3:20][C:17]([O:16][C:15](=[O:21])[N:14]([CH2:13][CH2:12][CH:11]([O:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Cl:1])[CH2:23][CH3:24])[CH3:22])([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 662,5-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 857904251,1-Dimethylethyl (3-hydroxypentyl)methylcarbamate

Product 1

HCID 86587540[3-(2,5-Dichlorophenoxy)pentyl]methylcarbamic acid, 1,1-dimethylethyl esterYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,5-Dichlorophenol (325 mg, 2.00 mmol) and (3-hydroxypentyl)methylcarbamic acid, 1,1-dimethylethyl ester (217 mg, 1.00 mmol) were dissolved in tetrahydrofuran (10 ml). To the resulting solution was added triphenylphosphine (393 mg, 1.50 mmol) and then diethyl azodicarboxylate (0.240 ml, 1.52 mmol). The solution was then allowed to stir at room temperature under nitrogen for 24 h. The mixture was then poured into water and extracted three times with diethyl ether. The combined organic fractions were washed with 1N sodium hydroxide solution twice and then brine and dried over magnesium sulfate. The solvent was evaporated and the residue eluted down a flash chromatography column using 10% ethyl acetate/isohexane as eluent to give 180 mg (50%) of the title compound as an oil.

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe combined organic fractions were washed with 1N sodium hydroxide solution twice
  3. dry with materialbrine and dried over magnesium sulfate
  4. customThe solvent was evaporated
  5. washthe residue eluted down a flash chromatography column

Sources & evidence

ORD record
ord-b503292cd0c642abb80dbe4e4a3af87c
Source dataset
uspto-grants-2005_05
Patent number
US06900243B2

Reaction notes

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