trans-Crotonyl chloride → (4R)-3-((E)-2-butenoyl)-4-(phenylmethyl)-2-oxazolidinone

HRID 842437

Reaction equation

[C:1]1([CH2:7][C@@H:8]2[CH2:12][O:11][C:10](=[O:13])[NH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:19](Cl)(=[O:23])/[CH:20]=[CH:21]/[CH3:22]>>[C:19]([N:9]1[C@H:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][O:11][C:10]1=[O:13])(=[O:23])/[CH:20]=[CH:21]/[CH3:22]

Participants

Reactant 3

HCID 643131trans-Crotonyl chloride

HCID 2734969(R)-4-Benzyl-2-oxazolidinone

HCID 178418339Butyllithium

Product 1

HCID 11481966(4R)-3-((E)-2-butenoyl)-4-(phenylmethyl)-2-oxazolidinone

Procedure

reacting (R)-4-(phenylmethyl)-2-oxazolidinone (5) with n-butyllithium and (E)-crotonyl chloride to produce (4R)-3-((E)-2-butenoyl)-4-(phenylmethyl)-2-oxazolidinone (6),

Sources & evidence

ORD record: ord-6fb62c4d13f4483392b6d44fac772611
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06375943B1

Linked notes

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