Dimethyl Sulfoxide → (1S)-2-azido-1-(3-chlorophenyl)ethan-1-ol
반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:21])[CH2:9]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=[CH:6][CH:7]=1.[N-:22]=[N+:23]=[N-:24].[Na+].CS(C)=O>O>[N:22]([CH2:9][C@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[OH:21])=[N+:23]=[N-:24]참가 물질
5
반응 조건
- 온도
- 80 °C
실험 절차
A mixture of toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester (16.34 g, 0.050 mol), sodium azide (6.50 g, 0.10 mol) and DMSO (50 mL) was stirred for 2 h at 80° C. Water (100 mL) was added, extracted with hexane-ether (1:1) mixture (2×150 mL). Combined extract was dried over Na2SO4, evaporated. The residue was separated on SiO2 (100 g), hexane-EtOAc, 0 to 20%. Colorless oil, 7.0 g, (0.035 mol, 71%).
후처리
- extractionextracted with hexane-ether (1:1) mixture (2×150 mL)
- extractionCombined extract
- dry with materialwas dried over Na2SO4
- customevaporated
- customThe residue was separated on SiO2 (100 g), hexane-EtOAc, 0 to 20%
출처 및 근거
- ORD 기록
- ord-513e7389f0af418aa86ac7879ec74dfb
- 출처 데이터셋
- uspto-grants-2011_11
- 특허 번호
- US08063225B2
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