Ethyl acetate hexane → 4-(5-Isopropoxy-2-methyl-4-nitrophenyl)cyclohex-3-enone

HRID 388574Notes

Reaction equation

HRID 388574 reaction equation
[CH:1]([O:4][C:5]1[C:6]([N+:22]([O-:24])=[O:23])=[CH:7][C:8]([CH3:21])=[C:9]([C:11]2[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH:12]=2)[CH:10]=1)([CH3:3])[CH3:2].CCCCCC.CCOC(C)=O>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:1]([O:4][C:5]1[C:6]([N+:22]([O-:24])=[O:23])=[CH:7][C:8]([CH3:21])=[C:9]([C:11]2[CH2:20][CH2:19][C:14](=[O:15])[CH2:13][CH:12]=2)[CH:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 597645528-(5-Isopropoxy-2-methyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Product 1

HCID 597643864-(5-Isopropoxy-2-methyl-4-nitrophenyl)cyclohex-3-enone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 8-(5-isopropoxy-2-methyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene (0.1 mmol) in 2.5 mL of TFA and CH2Cl2 (1:4 v/v), is stirred at room temperature for 6 hours. After workup and silica flash chromatography (hexane/EtOAc 4:1), 4-(5-isopropoxy-2-methyl-4-nitrophenyl)cyclohex-3-enone is obtained. 1H NMR (CDCl3, 400 MHz) δ 7.63 (s, 1H), 6.81 (s, 1H), 5.73 (m, 1H), 4.62 (m, 1H), 3.07 (m, 2H), 2.68 (m, 4H), 2.27 (s, 3H), 1.37 (d. 6H). MS (ES+): 290.13 (M+1)+.

Sources & evidence

ORD record
ord-4bb0d74e4f35473ba8466dbc872b94c4
Source dataset
uspto-grants-2013_02
Patent number
US08377921B2

Reaction notes

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