4-(2-Phenyleth-1-ynyl)thiophene-2-carbaldehyde → 4-(4-Chlorophenethyl)thiophene-3-carbaldehyde

HRID 1363253Notes

Reaction equation

HRID 1363253 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[C:11]([CH:15]=[O:16])=[CH:12][S:13][CH:14]=2)=[CH:4][CH:3]=1.C1(C#CC2C=C(C=O)SC=2)C=CC=CC=1.C(C1C=C(C=O)SC=1)CC1C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[C:11]([CH:15]=[O:16])=[CH:12][S:13][CH:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 27371394-(2-Phenyleth-1-ynyl)thiophene-2-carbaldehydeHCID 235874144-Phenethylthiophene-2-carbaldehydeHCID 723471274-[2-(4-Chlorophenyl)-vinyl]-thiophene-3-carbaldehyde

Product 1

HCID 596485314-(4-Chlorophenethyl)thiophene-3-carbaldehydeYield 72.1%

Procedure

4-(4-Chlorophenethyl)thiophene-3-carbaldehyde was synthesized from 4-[2-(4-chlorophenyl)-vinyl]-thiophene-3-carbaldehyde (260 mg, 1.04 mmol) following the conditions used to hydrogenate 4-(phenylethynyl)thiophene-2-carbaldehyde to 4-phenethylthiophene-2-carbaldehyde (Example 1.1.b). Purification by flash chromatography (0-10% EtOAc/heptane) yielded 4-(4-chlorophenethyl)thiophene-3-carbaldehyde (188 mg, 72%). 1H NMR (400 MHz, CDCl3) δ ppm 2.86-2.92 (m, 2H), 3.16-3.22 (m, 2H), 6.91 (dd, J=3.20, 0.82 Hz, 1H), 7.10-7.15 (m, 2H), 7.22-7.27 (m, 2H), 8.11 (d, J=3.11 Hz, 2H), 10.00 (d, J=0.82 Hz, 1H).

Workup

  1. customPurification by flash chromatography (0-10% EtOAc/heptane)

Sources & evidence

ORD record
ord-78242b86aea34040acfcd5189e3ca44b
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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