Triethylamine → Tert-butyl (4-{2-[(methylsulfonyl)oxy]ethyl}phenoxy)acetate

HRID 898889

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[CH:17][CH:18]=1)(=[O:29])=[O:28]

Participants

Conditions

Temperature: -10 °C

Procedure

Tert-butyl [4-(2-hydroxyethyl)phenoxy]acetate (6.000 g, 23.781 mmol) and triethylamine (9.9 ml, 71.341 mmol) were dissolved in DCM. The mixture was cooled to −10° C. and methanesulfonyl chloride (2.8 ml, 35.671 mmol) was added dropwise to the mixture. The reaction mixture was allowed to reach room temperature and was stirred for 16 hours. The mixture was diluted with DCM. The organic layer was washed with water, brine and 0.3M KHSO4, dried with MgSO4, and evaporated under reduced pressure. Obtained 7.5 g of light-yellow crystals (yield 95.5%).

Workup

customto reach room temperature
washThe organic layer was washed with water, brine and 0.3M KHSO4
dry with materialdried with MgSO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-645b4593cacc44a79a13e29e22ae538e
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351858B2

Linked notes

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