Potassium Hydroxide → (E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester

HRID 885893Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[C:12]([O:16][C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][N:21]=1)([CH3:15])([CH3:14])[CH3:13].[OH-].[K+]>CCO>[C:12]([O:16][C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:10]/[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=2)=[O:11])=[CH:22][N:21]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(4-hydroxymethyl-phenyl)-ethanone (750 mg, 5 mmol) in EtOH (15 ml) was added dropwise at 0° C. to a stirred solution of (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester (described in Example 11 STEP A-D, 1.16 g, 5 mmol) and 1.7 M KOH (4.4 ml) in EtOH (10 ml). The mixture was stirred at 0° C. for 5 h and the resulting precipitate was filtered and triturated with di-isopropylether to give 630 mg of desired (E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester. The mother liquors were diluted with water and extracted with AcOEt. The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was triturated with EtOH to give additional 70 mg of (E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester.

Workup

filtrationthe resulting precipitate was filtered
customtriturated with di-isopropylether

Sources & evidence

ORD record: ord-affe6ed0ebbf401793d5aac7c4011cce
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242175B2

Reaction notes

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