反応 #312605

ord-8ff353b74e004a86b005725840377b82

反応方程式

CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21
1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one
CCCCCC(O)c1ccc(N2C(OCc3ccc(C(=O)OC)s3)CCS2(=O)=O)cc1
alcohol
CCCCCC(O)c1ccc(N2C(OCc3ccc(C(=O)OC)s3)CCS2(=O)=O)cc1
Methyl 5-[({2-[4-(1-hydroxyhexyl)phenyl]-1,1 -dioxidoisothiazolidin-3-yl}oxy)methyl]thiophene-2-carboxylate
CCCCCC(=O)c1ccc(N2C(OCc3ccc(C(=O)OC)s3)CCS2(=O)=O)cc1
ketone
収率 101.2%
CCCCCC(=O)c1ccc(N2C(OCc3ccc(C(=O)OC)s3)CCS2(=O)=O)cc1
Methyl 5-({[2-(4-hexanoylphenyl)-1,1-dioxidoisothiazolidin-3-yl]oxy}methyl)thiophene-2-carboxylate
収率 101.2%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    ろ過filtered
  2. 2
    濃縮The filtrate was concentrated in vacuo and purification of the residue by flash column chromatography (silica gel, 1:1 hex/EtOAc)

実験手順

1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (44 mg, 0.104 mmol) was added to a solution of the alcohol 14 (42 mg, 0.087 mmol) in CH2Cl2 (2 mL) at 23° C. After stirring for 16 h the reaction mixture with CH2Cl2 and filtered. The filtrate was concentrated in vacuo and purification of the residue by flash column chromatography (silica gel, 1:1 hex/EtOAc) gave 41 mg (98%) of the ketone 16.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07557095B2uspto-grants-2009_07