1,2,3,4-Tetrahydro-2-naphthalenol → 4a-Methyl-4,4a,5,6-tetrahydro-2(3H)-naphthalenone

HRID 478070Notes

Reaction equation

[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[OH:11].[CH3:12]C(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>>[CH3:12][C:5]12[CH2:6][CH2:7][CH:8]=[CH:9][C:10]1=[CH:1][C:2](=[O:11])[CH2:3][CH2:4]2

Participants

Reactant 2

HCID 107471,2,3,4-Tetrahydro-2-naphthalenol

HCID 131709961Jones' reagent

Product 1

HCID 2774474a-Methyl-4,4a,5,6-tetrahydro-2(3H)-naphthalenone

Procedure

1,2,3,4-Tetrahydro-2-napthol is reduced according to Preparation 9. The resulting diene is cyclopropanated with Simmons-Smith reagent, oxidized with Jones reagent, then the cyclopropane ring opened with acid to form dienone 4.

Sources & evidence

ORD record: ord-5fcac40704fb4370b939c22b0213d194
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04889947

Reaction notes

Loading…