Triethylamine → Methyl 2-{[4-(3-{4-[(methylsulfonyl)oxy]phenoxy}propyl)phenoxy]methyl}benzoate

HRID 2112022Notes

Reaction equation

[OH:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:27]=[CH:26][C:13]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=3[C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[CH3:37][S:38]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:27]=[CH:26][C:13]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=3[C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)=[CH:28][CH:29]=1)(=[O:40])=[O:39]

Participants

Conditions

Temperature: -20 °C

Procedure

Methyl 2-({4-[3-(4-hydroxyphenoxy)propyl]phenoxy}methyl)benzoate (0.32 g, 0.81 mmol) was dissolved in dichloromethane (10 ml) and cooled to −20° C. Triethylamine (0.123 g, 1.22 mmol) was added drop wise and methanesulfonyl chloride (0.10 g, 0.89 mmol) was added drop wise. The ice bath was removed and the mixture was wormed to room temperature. Diethyl ether (5 ml) was added and the precipitate was filtered off. The organic phase was washed with two portions of brine (5 ml) and dried (MgSO4). Removing the solvent by evaporation gave 0.37 gram of methyl 2-{[4-(3-{4-[(methylsulfonyl)oxy]-phenoxy}propyl)phenoxy]methyl}benzoate (yield 97.3%).

Workup

customThe ice bath was removed
customwas wormed to room temperature
additionDiethyl ether (5 ml) was added
filtrationthe precipitate was filtered off
washThe organic phase was washed with two portions of brine (5 ml)
dry with materialdried (MgSO4)
customRemoving the solvent
customby evaporation

Sources & evidence

ORD record: ord-1a00703168db48169f1028b26374011d
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521461B2

Reaction notes

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