Dimethylformamide → 4-(1-Methylcyclopropyl)benzaldehyde

HRID 855270Notes

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.Br[C:13]1C=CC(C2(C)CC2)=CC=1.[Li]CCCC.CN(C=O)C>>[CH3:13][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 573742501-Bromo-4-(1-methylcyclopropyl)benzene

HCID 178418339Butyllithium

Product 1

HCID 860938474-(1-Methylcyclopropyl)benzaldehydeYield 80%

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 1-bromo-4-(1-methylcyclopropyl)-benzene (2.10 g, 9.95 mmol), nBuLi (9.33 ml, 1.6M solution in hexane, 14.92 mmol) and DMF (3.87 ml, 49.74 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 4-(1-methylcyclopropyl)-benzaldehyde (1.28 g, 80%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): 9.96 (s, 1H), 7.79 (d, J=8.5 Hz, 2H), 7.37 (d, J=8.5 Hz, 2H), 1.46 (s, 1H), 0.98-0.93 (m, 2H), 0.90-0.84 (m, 2H).

Workup

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

Sources & evidence

ORD record: ord-bde83f2e0c36477bb5041710a9b7c291
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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