Ethyl Acetate → Methyl 2-({2-[4-(2-tert-butoxy-2-oxoethoxy)phenyl]ethyl}thio)benzoate

HRID 898929

Reaction equation

CS(O[CH2:6][CH2:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:10][CH:9]=1)(=O)=O.[SH:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>C(#N)C>[C:17]([O:16][C:14](=[O:15])[CH2:13][O:12][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][S:23][C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=1)([CH3:18])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 60 °C

Procedure

Tert-butyl (4-{2-[(methylsulfonyl)oxy]ethyl}phenoxy)acetate (5.454 g, 17.347 mmol) was dissolved in acetonitrile (100 ml), methyl 2-mercaptobenzoate (3.502 g, 20.816 mmol) and dipotassium carbonate (4.795 g, 34.694 mmol) was added. The solution was stirred for 10 hours at 60° C. EtOAc (40 ml) was added and the organic phase was washed with two portions of brine (2×40 ml, aq). The organic layer was dried (MgSO4) and the solvent was removed by evaporation to give 6.931 g crude of methyl 2-({2-[4-(2-tert-butoxy-2-oxoethoxy)phenyl]ethyl}thio)benzoate. The crude was used in the next step without further purification.

Workup

washthe organic phase was washed with two portions of brine (2×40 ml, aq)
dry with materialThe organic layer was dried (MgSO4)
customthe solvent was removed by evaporation

Sources & evidence

ORD record: ord-a683bfe9dc8244a3a7b20ca567be503e
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351858B2

Linked notes

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