Methanol → 2-(1,1-Dimethylethyl)-N-ethyl-N-(1-methoxy-2,2-dimethylpropyl)benzamide

A mixture of 2-tert-butylbenzoic acid (15.7 g, 88.2 mmol) and thionyl chloride (19.3 mL, 265 mmol) was stirred at RT for 1 day, then was concentrated and stripped from toluene (2X) under vacuum. The compound from example k (19.94 g, 176.5 mmol) was added to a solution of this crude 2-tert-butylbenzoyl chloride in toluene (90 mL), and the mixture was heated at 100° C. for 3 h, then was stirred at room temperature overnight. The resulting mixture was cooled with an ice-water bath, and Et3N (13.4 g, 132.4 mmol) was added, followed by the dropwise addition of methanol (5.65 g, 176.6 mmol). The resulting reaction mixture was stirred at RT and monitored to completion by GLC, then was partitioned between ether and sat aq NaHCO3. The ether extract was dried (MgSO4), concentrated, and purified by flash chromatography with 1:9 EtOAc/hexanes to afford 20.8 g of the title compound as a pale yellow oil, a 77% yield.

1. concentrationwas concentrated
2. temperaturethe mixture was heated at 100° C. for 3 h
3. stirringwas stirred at room temperature overnight
4. temperatureThe resulting mixture was cooled with an ice-water bath
5. customThe resulting reaction mixture
6. stirringwas stirred at RT
7. customwas partitioned between ether
8. extractionThe ether extract
9. dry with materialwas dried (MgSO4)
10. concentrationconcentrated
11. custompurified by flash chromatography with 1:9 EtOAc/hexanes

ORD record

ord-cd4718ded6544db18dea2575e9b7f5a3

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05834447