Dimethylformamide → 4-(1-Methoxycyclopropyl)-benzaldehyde

HRID 2244318Notes

Reaction equation

[CH:1]1([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.BrC1C=CC([C:19]2([O:22]C)CC2)=CC=1.[Li]CCCC.CN(C=O)C>>[CH3:19][O:22][C:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:8]=[O:9])=[CH:10][CH:11]=2)[CH2:2][CH2:3]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 115064744-Cyclopropylbenzaldehyde

HCID 22568990HCID 22568990, compound

HCID 178418339Butyllithium

Product 1

HCID 860937274-(1-Methoxycyclopropyl)-benzaldehydeYield 58%

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S1-A) using 1-bromo-4-(1-methoxycyclopropyl)-benzene (250 mg, 1.10 mmol), n-BuLi (722 μl, 1.6M solution in hexane, 1.16 mmol) and DMF (171 μl, 2.20 mmol). The isolated residue was purified by flash column chromatography (1:9 ether/pentane) to give 4-(1-methoxycyclopropyl)-benzaldehyde (90 mg, 58%) as a colourless oil. 1H NMR (CDCl3, 300 MHz): δ 10.0 (s, 1H), 7.79 (d, J=8.5 Hz, 2H), 7.37 (d, J=8.5 Hz, 2H), 3.29 (s, 3H), 1.35-1.30 (m, 2H), 1.09-1.05 (m, 2H).

Workup

customThe isolated residue was purified by flash column chromatography (1:9 ether/pentane)

Sources & evidence

ORD record: ord-4a131904db024239873db749ee4f23be
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678818B2

Reaction notes

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