2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 70655284, compound

HRID 879119Notes

Reaction equation

HRID 879119 reaction equation
C(O[B:5]1[O:9][C:8]([CH3:11])([CH3:10])[C:7]([CH3:13])([CH3:12])[O:6]1)(C)C.C([Li])CCC.[F:19][C:20]1[CH:21]=[C:22]([CH:30]=[C:31]([F:33])[CH:32]=1)[O:23][CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[F:33][C:31]1[CH:30]=[C:22]([O:23][CH:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[CH:21]=[C:20]([F:19])[C:32]=1[B:5]1[O:6][C:7]([CH3:12])([CH3:13])[C:8]([CH3:10])([CH3:11])[O:9]1

Participants

4

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 70655188HCID 70655188, compoundHCID 178418339Butyllithium

Product 1

HCID 70655284HCID 70655284, compoundYield 33%

Procedure

Method 3 was followed using 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.5 equiv.), butyllithium (1.3 equiv.) and 4-(3,5-difluorophenoxy)tetrahydro-2H-pyran (1.0 equiv.) to give 2-(2,6-difluoro-4-((tetrahydro-2H-pyran-4-yl)oxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in 33% yield. 1H NMR (400 MHz, <cdcl3>) δ ppm 1.21-1.34 (m, 12H), 1.78 (dtd, J=12.72, 8.31, 8.31, 3.91 Hz, 2H), 1.93-2.09 (m, 2H), 3.59 (ddd, J=11.64, 8.31, 3.13 Hz, 2H), 3.89-4.01 (m, 2H), 4.48 (tt, J=7.78, 3.77 Hz, 1H), 6.40 (d, J=9.39 Hz, 2H).

Sources & evidence

ORD record
ord-35854343d78c43b9b8f1b9dc6a5787be
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

Loading…