Tetrahydrofuran → HCID 89768078, compound

HRID 591503Notes

Reaction equation

[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[C:10]([CH2:13][C:14]([NH2:16])=[O:15])=[CH:11][S:12][C:8]=2[CH:7]=1.C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:39][S:40](Cl)(=[O:42])=[O:41]>O>[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[C:10]([CH2:13][C:14]([NH:16][S:40]([CH3:39])(=[O:42])=[O:41])=[O:15])=[CH:11][S:12][C:8]=2[CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a mixture of 2-(6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetamide (73.3 mg) and THF (dry) (10 mL) was added sodium bis(trimethylsilyl)amide (0.158 ml, 1.9 M in toluene) at −78° C. The mixture was stirred at −40° C. under argon atmosphere for 30 min. And then methanesulfonyl chloride (34.4 mg) was added thereto. The resulting mixture was stirred at room temperature under argon atmosphere overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (11.00 mg).

Workup

stirringThe resulting mixture was stirred at room temperature under argon atmosphere overnight
extractionextracted with EtOAc
customThe organic layer was separated
washwashed successively with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record: ord-6c2c50998dce4d949a6e4dc2286ecea1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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