Dimethylformamide → 4-(1-Methoxycyclobutyl)benzaldehyde

HRID 855289Notes

Reaction equation

C1(C2C=CC([CH:8]=[O:9])=CC=2)CC1.Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([O:23][CH3:24])[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[Li]CCCC.CN(C=O)C>>[CH3:24][O:23][C:19]1([C:16]2[CH:17]=[CH:18][C:13]([CH:8]=[O:9])=[CH:14][CH:15]=2)[CH2:22][CH2:21][CH2:20]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 115064744-Cyclopropylbenzaldehyde

HCID 671435241-Bromo-4-(1-methoxycyclobutyl)benzene

HCID 178418339Butyllithium

Product 1

HCID 860937504-(1-Methoxycyclobutyl)benzaldehydeYield 69%

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 1-bromo-4-(1-methoxycyclobutyl)-benzene (140 mg, 0.58 mmol), n-BuLi (363 μl, 1.6M solution in hexane, 0.58 mmol) and DMF (90 μl, 1.16 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 4-(1-methoxycyclobutyl)-benzaldehyde (76 mg, 69%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 10.03 (s, 1H), 7.91 (d, J=8.5 Hz, 2H), 7.61 (d, J=8.5 Hz, 2H), 2.96 (s, 3H), 2.45-2.39 (m, 4H), 1.99 (m, 1H), 1.73 (m, 1H).

Workup

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

Sources & evidence

ORD record: ord-d217928f907f4e96aec89c4afad14b43
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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