HRID1768703

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11776

Triphenylphosphine

C18H15P

HCID5462977

(E)-Diethyl azodicarboxylate

C6H10N2O4

结构：CC(C)c1cc(O)cc2c1C(=O)N(CSc1ccccc1)S2(=O)=O

HCID10316654

未命名化合物

HCID12012172

未命名化合物

PRODUCTS

生成物

结构：CC(C)c1cc(OCCO[Si](C(C)C)(C(C)C)C(C)C)cc2c1C(=O)N(CSc1ccccc1)S2(=O)=O

HCID69959552

未命名化合物

收率 86%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

To a solution of 4-isopropyl-6-hydroxy-2-phenylthiomethylsaccharin. (2.0 g, 5.509 mmol) in THF (35 mL) containing triphenylphosphine (1.59 g, 6.06 mmol) and 2-(triisopropylsilyloxy) ethanol (1.13 g, 6.0 mmol) at room temperature was added diethylazodicarboxylate (1.04 mL, 6.6 mmol). The mixture was stirred overnight (16 hours), the solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 10% ethyl acetate/hexane to afford 2.66 g (86%) of 4-isopropyl-6-[2-(triisopropylsilyloxy)ethoxy]-2-phenylthiomethylsaccharin as an oil.

WORKUP

后处理

customthe solvent was removed in vacuo
customthe residue was purified by column chromatography on silica eluting with 10% ethyl acetate/hexane

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ca29225ea9734d51aa9a935c18918fac
来源数据集: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05378720
来源说明: uspto-grants-1995_01

反应 SMILES

[CH:1]([C:4]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]2[C:5]=1[C:6](=[O:24])[N:7]([CH2:16][S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:44]([Si:47]([CH:55]([CH3:57])[CH3:56])([CH:52]([CH3:54])[CH3:53])[O:48][CH2:49][CH2:50]O)([CH3:46])[CH3:45].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:1]([C:4]1[CH:14]=[C:13]([O:15][CH2:50][CH2:49][O:48][Si:47]([CH:52]([CH3:53])[CH3:54])([CH:44]([CH3:46])[CH3:45])[CH:55]([CH3:56])[CH3:57])[CH:12]=[C:11]2[C:5]=1[C:6](=[O:24])[N:7]([CH2:16][S:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2]