Sodium Iodide → 3-(5-Methyl-thiophen-2-ylmethyl)-benzaldehyde

HRID 1927273Notes

Reaction equation

C(#N)C.[I-].[Na+].C[Si](Cl)(C)C.[O:11]1CCO[CH:12]1[C:16]1[CH:17]=[C:18]([CH:22]([C:24]2[S:25][C:26]([CH3:29])=[CH:27][CH:28]=2)O)[CH:19]=[CH:20][CH:21]=1>O>[CH3:29][C:26]1[S:25][C:24]([CH2:22][C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=2)[CH:12]=[O:11])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of acetonitrile (20 mL) and sodium iodide (2.9 g) was added trimethylsilyl chloride (2.1 g) at room temperature under stirring. The reaction solution thus obtained was cooled to −20° C., and (3-[1,3]dioxolan-2-yl-phenyl)-(5-methyl-thiophen-2-yl)-methanol (1.1 g) described in Manufacturing Example 52-1 and acetonitrile (5 mL) were added thereto under stirring. The reaction solution was returned to room temperature and stirred for 10 minutes. Water was added to the reaction solution, which was then extracted with ethyl acetate. The solvent was evaporated from the organic layer under a reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1) to obtain the titled compound (360 mg).

Workup

customThe reaction solution thus obtained
additionwere added
stirringunder stirring
customwas returned to room temperature
stirringstirred for 10 minutes
extractionwas then extracted with ethyl acetate
customThe solvent was evaporated from the organic layer under a reduced pressure
customthe residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-aa53d48dc8ae4cfda36614f900f62de3
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183264B2

Reaction notes

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