Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]hept-5-ene-2-carboxylate → Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexa-1,3-dienecarboxylate

HRID 1401036Notes

Reaction equation

HRID 1401036 reaction equation
[CH3:1][C:2]1([CH3:20])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH2:19][C:11]3([CH2:14][CH:13]([C:15](OC)=O)C3)C=2)[O:3]1.FC(F)(F)S(OC1CCC([C:33]([O:35][CH3:36])=[O:34])=CC=1)(=O)=O>>[CH3:20][C:2]1([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH2:19][CH2:11][C:14]([C:33]([O:35][CH3:36])=[O:34])=[CH:13][CH:15]=2)[O:3]1

Participants

3

Reactant 2

HCID 86692319Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]hept-5-ene-2-carboxylateHCID 86692395HCID 86692395, compound

Product 1

HCID 86692396Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexa-1,3-dienecarboxylateYield 46.6%

Procedure

The title compound was prepared following the method described in step 2 for the preparation of methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]hept-5-ene-2-carboxylate, using methyl 4-(((trifluoromethyl)sulfonyl)oxy)cyclohexa-1,3-dienecarboxylate as the reactant. (46.6% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.00 (dt, J=5.3, 1.5 Hz, 1H), 6.75 (dt, J=5.3, 1.6 Hz, 1H), 3.74 (s, 3H), 2.42-2.35 (m, 2H), 2.34-2.27 (m, 2H), 1.26 (s, 12H).

Sources & evidence

ORD record
ord-710b1c5d59b648b79f94fec248d17430
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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