Dimethylformamide → p-Cyclopentylbenzaldehyde

HRID 855328Notes

Reaction equation

HRID 855328 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.BrC1C=CC(C2CCCC=2)=CC=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

7

Reactant 6

HCID 6228DimethylformamideHCID 8058HexaneHCID 115064744-CyclopropylbenzaldehydeHCID 115286721-Bromo-4-cyclopentenylbenzeneHCID 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 S53) using 720 mg of a mixture of 1-bromo-4-cyclopentyl-benzene and 1-bromo-4-cyclopent-1-enyl-benzene (˜3.2 mmol), 2.2 ml of a 1.6 molar solution of n-BuLi in hexane (3.52 mmol) and 492 μl of DMF (6.40 mmol). 4-Cyclopentyl-benzaldehyde was isolated by flash column chromatography (5:95 EtOAc/c-hexane) as a yellow liquid (165 mg, 30%). 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-b842348a4ffc4d9bbdae9b695042b56d
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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