Ethanol → HCID 54706616, compound

HRID 1166590Notes

Reaction equation

C=C[C@@H]1[C@@H]2C[C@@H]([C@H:11]([OH:22])C3C4C(=CC=CC=4)N=CC=3)N(CC2)C1.[C:23]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=1.ClC1C=CC(C2C=CC(C=[O:51])=CC=2)=CC=1.[CH3:52][CH2:53][OH:54]>>[C:23]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:24]=[CH:25][C:26]([CH:29]2[O:30][C:53](=[O:54])[C:52]([OH:51])=[C:11]2[OH:22])=[CH:27][CH:28]=1

Participants

Reactant 4

HCID 702Ethanol

HCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

HCID 101744Cinchonidine

HCID 5925704'-Chloro[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 54706616HCID 54706616, compound

Procedure

Solvents were of commercial quality and were used as received. (−)-Cinchonidine {96%; [α]23=−109.2° (c=1.5; EtOH)} was purchased from Aldrich Chemical and used as such. 5-[(1,1′-biphenyl)-4-yl]-3,4-dihydroxy-2(5H)-furanone and 5-[(4′-chloro-1,1′-biphenyl)-4-yl]-3,4-dihydroxy-2(5H)-furanone were prepared according to Dahn's method 1,2,3,4,5 starting, respectively, from biphenyl-4-carboxaldehyde and 4′-chlorobiphenyl-4-carboxaldehyde 6.

Sources & evidence

ORD record: ord-fd67759abe13431a88fee9623ab9e8d6
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613919B2

Reaction notes

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