Tetrahydrofuran → HCID 28561511, compound

HRID 1927257Notes

Reaction equation

HRID 1927257 reaction equation
C1COCC1.C[O:7][C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:11][CH:10]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][OH:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2416604Methyl 4-(pyridin-2-ylmethoxy)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 28561511HCID 28561511, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of THF (50 mL) of 4-(pyridin-2-ylmethoxy)-benzoic acid methyl ester (4.9 g) described in Manufacturing Example 25-1 was added LAH (1.0 g) at 0° C., which was stirred for 20 minutes at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was concentrated and purified by silica gel chromatography (heptane:ethyl acetate=1:1, then ethyl acetate) to obtain the titled compound (1.6 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel chromatography (heptane

Sources & evidence

ORD record
ord-f80c8da52b65448691665c7f621441da
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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