1,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate → 8-(5-Isopropoxy-2-methyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene
Reaction equation
FC(F)(F)S(O[C:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH:8]=1)(=O)=O.[CH:19]([O:22][C:23]1[C:24]([N+:39]([O-:41])=[O:40])=[CH:25][C:26]([CH3:38])=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:28]=1)([CH3:21])[CH3:20].[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.CCCCCC.CCOC(C)=O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]([O:22][C:23]1[C:24]([N+:39]([O-:41])=[O:40])=[CH:25][C:26]([CH3:38])=[C:27]([C:7]2[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH:8]=2)[CH:28]=1)([CH3:21])[CH3:20]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A stirred solution of the 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (0.03 mmol) and 2-(5-isopropoxy-2-methyl-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Intermediate 5, 0.04 mmol) in THF (3 mL), containing [Pd(PPh3)4] (0.013 mmol) and K3PO4.H2O (0.045 mmol), is heated to 80° C. under argon for 16 hours. After workup and silica flash chromatography (hexane/EtOAc 4:1), 8-(5-isopropoxy-2-methyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene is obtained. 1H NMR (CDCl3, 400 MHz) δ 7.62 (s, 1H), 6.82 (s, 1H), 5.74 (m, 1H), 4.65 (m, 1H), 4.04 (m, 4H), 2.47 (m, 4H), 2.27 (s, 3H), 1.89 (t, 2H), 1.29 (d, 6H). MS (ES+): 334.16 (M+1)+.
Sources & evidence
- ORD record
- ord-66582ec1128c4a528215a94c9fbda04b
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399450B2
Reaction notes
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