Multi-step reaction with 10 steps
1.1: triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 22 h / 26 °C / Cooling
2.1: oxalyl dichloride / N,N-dimethyl-formamide; toluene / 4 h / 20 °C
3.1: ethylmagnesium bromide / toluene; chlorobenzene; diethyl ether / 1.02 h / -4 - 2.5 °C
3.2: 5.75 h / 2 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 57 h / 20 °C
5.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 17 h / 2 - 20 °C
6.1: methanol; sodium hydroxide / tetrahydrofuran; water / 2 h
7.1: lithium borohydride / tetrahydrofuran / 2.61 h
7.2: 16 h
8.1: dmap / dichloromethane / 16 h / 20 °C
9.1: trifluoroacetic acid / ethyl acetate / 4.75 h / 2 - 4 °C
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / ethyl acetate / 3 h
With
methanol; dmap; lithium borohydride; oxalyl dichloride; di-isopropyl azodicarboxylate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; chlorobenzene; toluene;