Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]hept-5-ene-2-carboxylate → HCID 86692380, compound

HRID 1401023Notes

Reaction equation

HRID 1401023 reaction equation
[CH3:1][C:2]1([CH3:20])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH2:19]C3(CC(C(OC)=O)C3)[CH:10]=2)[O:3]1.[CH3:21][C:22]1[CH:23]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:24]C=C(OS(C(F)(F)F)(=O)=O)C=1>>[CH3:21][C:22]1[CH:10]=[C:9]([B:4]2[O:3][C:2]([CH3:20])([CH3:1])[C:6]([CH3:8])([CH3:7])[O:5]2)[CH2:19][CH2:24][C:23]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]

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 86692379Ethyl 2-methyl-4-(((trifluoromethyl)sulfonyl)oxy)cyclohexa-2,4-dienecarboxylate

Product 1

HCID 86692380HCID 86692380, compoundYield 57.8%

Procedure

The title compound was prepared following the method 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, Step 2 described above in page 65-67, using ethyl 2-methyl-4-(((trifluoromethyl)sulfonyl)oxy)cyclohexa-2,4-dienecarboxylate as the reactant. (57.8% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 6.64 (t, J=1.6 Hz, 1H), 4.28-4.15 (m, 2H), 2.46-2.32 (m, 2H), 2.29-2.19 (m, 2H), 2.18 (t, J=1.8 Hz, 3H), 1.38-1.25 (m, 15H).

Sources & evidence

ORD record
ord-ccbd9fe2d5c942bfa9d8a2c85de0da1f
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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