O-Allylhydroxylamine hydrochloride → (2E)-3-(4-{[(benzyloxy)imino]methyl}phenyl)acrylic acid

HRID 1160237Notes

Reaction equation

[CH:1]([C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=O.Cl.[CH2:15]([O:18][NH2:19])[CH:16]=[CH2:17]>CN(C=O)C.CCOC(C)=O>[CH2:15]([O:18][N:19]=[CH:1][C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)[C:16]1[CH:5]=[CH:4][CH:3]=[CH:1][CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

a solution of trans 4-formyl-cinnamic acid A (Y═CH═CH, R1, ═H, R3═H, 0.346 g, 1.96 mmol.) and B O-Allylhydroxylamine hydrochloride (0.258 g, 2.37 mmol.) dissolved in 2 mL of DMF was warmed at 50° C. and stirred for 5 h. Then the solution was diluted with AcOEt and washed with water. Organic layer was dried on Na2SO4 and then concentrated under reduced pressure to give 0.421 g of the intermediate C (2E)-3-(4-{[(benzyloxy)imino]methyl}phenyl)acrylic acid (93% yield).

Workup

washwashed with water
customOrganic layer was dried on Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6143b40f096a43f0a2d97efec30075e6
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816386B2

Reaction notes

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