Triethylamine → HCID 86601925, compound

HRID 2112010Notes

Reaction equation

[OH:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH2:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[O:12][CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[CH3:36][S:37]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[O:12][CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:27][CH:28]=1)(=[O:39])=[O:38]

Participants

Conditions

Temperature: -20 °C

Procedure

Methyl 2-({3-[2-(4-hydroxyphenoxy)ethyl]phenoxy}methyl)benzoate (0.096 g, 0.25 mmol) was dissolved in dichloromethane (10 ml) and cooled to −20° C. Triethylamine (0.039 g, 0.38 mmol) was added drop wise and methanesulfonyl chloride (0.032 g, 0.28 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 filtered off. The organic phase was washed with two portions of brine (5 ml) and dried (MgSO4). Removing The solvent was removed by evaporation giving 0.109 gram of methyl 2-{[3-(2-{4-[(methylsulfonyl)oxy]phenoxy}-ethyl)phenoxy]methyl}benzoate (yield 94.1%).

Workup

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

Sources & evidence

ORD record: ord-cd6281af9e7b4edfbb5d84a3d3f3845b
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521461B2

Reaction notes

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