Tetrahydrofuran → 2-Cyclopropyl-6-ethyl-benzaldehyde

HRID 1694803Notes

Reaction equation

HRID 1694803 reaction equation
C(/N=[CH:6]/[C:7]1[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1Cl)CCC.[CH:16]1([Mg]Br)[CH2:18][CH2:17]1.[O:21]1CCCC1>CCOCC.[Cl-].[Mn+2].[Cl-]>[CH:16]1([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([CH2:13][CH3:14])[C:7]=2[CH:6]=[O:21])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 178418630HCID 178418630, compoundHCID 178448975HCID 178448975, compound

Product 1

HCID 589519652-Cyclopropyl-6-ethyl-benzaldehyde

Reagents, catalysts & solvents 2

HCID 10313134Manganese(2+) dichlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Prepared in analogy to Example 57(c) from butyl-[1-(2-chloro-6-ethyl-phenyl)-meth-(E)-ylidene]-amine, cyclopropylmagnesium bromide and manganese(II) chloride in tetrahydrofuran and ether followed by chromatography on silical gel. Yellow oil. 1H-NMR (CDCl3): 0.74 (2H, m, CH2), 1.02 (2H, m, CH2), 1.25 (3H, t, CH3), 2.40 (1H, m, CH), 2.98 (2H, q, CH2), 7.04 (1H, d, ArH), 7.12 (1H, d, ArH), 7.36 (1H, dd, ArH), 10.9 (1H, s, CHO).

Sources & evidence

ORD record
ord-b4a29dab21794e61b2b7c887475641cf
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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