Styrylboronic acid → (E)-5-styrylthiophene-3-carbaldehyde

HRID 1363260Notes

Reaction equation

HRID 1363260 reaction equation
I[C:2]1[S:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.[CH:9](/B(O)O)=[CH:10]\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.ClC1C=CC(CC2C=C(C=O)SC=2)=CC=1>>[CH:9](/[C:2]1[S:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1)=[CH:10]\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 5702628Styrylboronic acidHCID 217668865-Iodothiophene-3-carbaldehydeHCID 596485254-(4-Chlorobenzyl)thiophene-2-carbaldehyde

Product 1

HCID 59648535(E)-5-styrylthiophene-3-carbaldehydeYield 20%

Procedure

(E)-5-styrylthiophene-3-carbaldehyde was synthesized from 5-iodo-3-thiophene carboxaldehyde and (E)-styrylboronic acid using the conditions to synthesize 4-(4-chlorobenzyl)thiophene-2-carbaldehyde. The crude product was chromatographed over silica gel (0 to 25% EtOAc in heptane over 30 min) to give (E)-5-styrylthiophene-3-carbaldehyde (0.115 g, 20% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.86 (s, 1H), 7.97 (s, 1H), 7.48 (m, 3H), 7.38 (m, 2H), 7.31 (m, 1H), 7.19 (d, J=16.2 Hz, 1H), 6.99 (d, J=16.2 Hz, 1H).

Workup

  1. customThe crude product was chromatographed over silica gel (0 to 25% EtOAc in heptane over 30 min)

Sources & evidence

ORD record
ord-361ab78995a34d47afb74d39d7deffe4
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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