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

HRID 2422249Notes

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

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-tetrahydrofuran (60-30 mL) and cooled to 0° C., and diethyl azodicarboxylate (40% toluene solution, 15.2 g) was added dropwise with vigorously stirring. After the completion of the dropwise addition, the temperature of the reaction mixture was allowed to return to room temperature and the mixture was further stirred for 1 hr. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:19 to 1:1 by volume ratio) to give the title compound (5.19 g, yield 54%) as colorless crystals.

Workup

additionAfter the completion of the dropwise addition
customto return to room temperature
stirringthe mixture was further stirred for 1 hr
concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:19 to 1:1 by volume ratio)

Sources & evidence

ORD record: ord-cbbdd78b78194abdac92ca3bc668b8b9
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960369B2

Reaction notes

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