Aluminium lithium hydride → 5-(2-Morpholin-4-yl-ethyloxy)benzofuran-2-carbaldehyde

HRID 751453Notes

Reaction equation

HRID 751453 reaction equation
COCN[C:5]([C:7]1[O:8][C:9]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:12][C:10]=2[CH:11]=1)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:19]1([CH2:18][CH2:17][O:16][C:13]2[CH:14]=[CH:15][C:9]3[O:8][C:7]([CH:5]=[O:6])=[CH:11][C:10]=3[CH:12]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 572471665-(2-Morpholin-4-yl-ethyloxy)benzofuran-2-carboxylic acid methoxy methyl amide

Product 1

HCID 229283565-(2-Morpholin-4-yl-ethyloxy)benzofuran-2-carbaldehydeYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-(2-morpholin-4-yl-ethyloxy)benzofuran-2-carboxylic acid methoxy methyl amide (0.2 g) of Example 20a in THF was added LAH (2.0 mL of a 1 M solution in THF). The reaction was stirred until complete consumption of the starting material. Workup gave 160 mg of the title compound.

Sources & evidence

ORD record
ord-31154a96b96348acbfc47cd6f49f4bc3
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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