Dimethylformamide → p-Cyclopentylbenzaldehyde

HRID 2244312Notes

Reaction equation

HRID 2244312 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(C2CCCC2)=C[CH:14]=1.[Li]CCCC.CCCCCC.CN(C=O)C>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:8]=[O:9])=[CH:10][CH:11]=2)[CH2:3][CH2:2][CH2:14][CH2:13]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8058HexaneHCID 115064744-CyclopropylbenzaldehydeHCID 543241331-Bromo-4-cyclopentylbenzeneHCID 178418339Butyllithium

Product 1

HCID 3016187p-Cyclopentylbenzaldehyde

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S1-A) using 2.07 g of 1-bromo-4-cyclopentyl-benzene (9.2 mmol), 6.32 ml of a 1.6 molar solution of n-BuLi in hexane (10.11 mmol) and 1.422 ml of DMF (18.4 mmol). 4-Cyclopentyl-benzaldehyde was isolated by flash column chromatography (5:95 EtOAc/c-hexane) as a colorless liquid (1146 mg, 72%). 1H NMR (CDCl3, 300 MHz): δ 1.53-1.91 (m, 6H), 2.11 (m, 2H), 3.07 (quint, J=8.5 Hz, 1H), 7.40 (d, J=8 Hz, 2H), 7.80 (d, J=8 Hz, 2H), 9.97 (s, 1H).

Sources & evidence

ORD record
ord-c4747a1348f14e99bded1592e7a49af3
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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