Triphenylphosphine → Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoate

HRID 732169Notes

Reaction equation

HRID 732169 reaction equation
[Cl:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.O[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.O1CCCC1>[Cl:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:8][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoateYield 54.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(Chloromethyl)benzyl alcohol (4.68 g), methyl 3-(4-hydroxyphenyl)propanoate (5.40 g) and triphenylphosphine (9.20 g) were dissolved in a mixed solvent of toluene (60 mL)-tetrahydrofuran (30 mL), cooled to 0° C. and diethyl azodicarboxylate (40% toluene solution, 15.2 g) was added dropwise with stirring. After completion of the dropwise addition, the reaction mixture was allowed to warm to room temperature and further stirred for 1 hr. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:1 in volume ratio) to give the title compound (5.19 g, yield 54%) as colorless crystals.

Workup

  1. additionAfter completion of the dropwise addition
  2. temperatureto warm to room temperature
  3. stirringfurther stirred for 1 hr
  4. concentrationThe reaction mixture was concentrated
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:1 in volume ratio)

Sources & evidence

ORD record
ord-19621889de004c10928827016421ca4e
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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