5-Hydroxy-1-tetralone → oxirane (S)-5-(2,3-epoxypropoxy)-3,4-dihydro-1(2H)-naphthalenone

HRID 22086

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[CH2:13]([C@@H:15]1[O:17][CH2:16]1)Cl>>[O:17]1[CH2:16][C@H:15]1[CH2:13][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[O:12]1[CH2:7][CH2:8]1

Participants

Reactant 2

HCID 1199215-Hydroxy-1-tetralone

HCID 2734062(-)-Epichlorohydrin

Product 1

HCID 86748747oxirane (S)-5-(2,3-epoxypropoxy)-3,4-dihydro-1(2H)-naphthalenone

Procedure

reacting 5-hydroxy-3,4-dihydro-1(2H)-naphthalenone with (R)-(-)-epichlorhydrine, in an aprotic solvent in the presence of a strong base at a temperature of over 90° C., to give the intermediate chiral oxirane (S)-5-(2,3-epoxypropoxy)-3,4-dihydro-1(2H)-naphthalenone with an optical purity greater than 95%, and then,

Sources & evidence

ORD record: ord-7d47044e2ac44991bb2f6c1fec64c091
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05426227

Linked notes

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