Dimethylformamide → 2-(2-Ethyl-[1,3]dioxolan-2-yl)thiophene-4-carbaldehyde

HRID 49350Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:7]2([CH2:12][CH3:13])[O:11][CH2:10][CH2:9][O:8]2)[S:5][CH:6]=1.C([Li])CCC.CN(C)[CH:21]=[O:22]>>[CH2:12]([C:7]1([C:4]2[S:5][CH:6]=[C:2]([CH:21]=[O:22])[CH:3]=2)[O:11][CH2:10][CH2:9][O:8]1)[CH3:13]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 179347332-(4-Bromothiophen-2-yl)-2-ethyl-1,3-dioxolane

HCID 178418339Butyllithium

Product 1

HCID 179348042-(2-Ethyl-[1,3]dioxolan-2-yl)thiophene-4-carbaldehyde

Procedure

In a manner similar to that of Example 9(g), by reaction of 12 g (45.6 mmol) of 2-(4-bromo-2-thienyl)-2-ethyl-[1,3]dioxolane with 20 mL (50 mmol) of 2.5 M butyllithium and 3.9 mL (50 mmol) of dimethylformamide, the desired product is obtained in the form of a yellow oil (m=4.6 g, Y=48%).

Sources & evidence

ORD record: ord-314cddafb6cf49a39ef4ccc152e41053
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Reaction notes

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