HCID 67515231, compound → HCID 67515287, compound

HRID 1754337Notes

Reaction equation

HRID 1754337 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]([OH:14])[C:12]3([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]>[O-2].[O-2].[O-2].[Cr+6]>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13](=[O:14])[C:12]3([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

3

Reactant 1

HCID 67515231HCID 67515231, compound

Product 1

HCID 67515287HCID 67515287, compound

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst

Procedure

The crude product was purified with column chromatography (silica gel, ethyl acetate and hexane) to afford the desired product 170 mg of the title product along with 100 mg of the 3-(3-bromo-4-methylphenyl)-1-oxa-2-azaspiro[4.5]dec-2-en-4-ol. The 3-(3-bromo-4-methylphenyl)-1-oxa-2-azaspiro[4.5]dec-2-en-4-ol was again converted to the title product by the oxidation with chromium trioxide by following the procedure described for step-5 of the intermediate 1.

Sources & evidence

ORD record
ord-30a64e084a2c49afac94c03f11091a6a
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

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