2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 68315186, compound

HRID 2202137Notes

Reaction equation

HRID 2202137 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9](C)([CH2:11][CH2:12][CH2:13][CH2:14]C)C)[CH:6]=[C:5]([O:17][CH3:18])[C:4]=1[B:19]1[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]1.[Li]CCCC.B1(OC(C)C)OC(C)(C)C(C)(C)O1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:11][CH2:12][CH2:13][CH3:14])[CH:6]=[C:5]([O:17][CH3:18])[C:4]=1[B:19]1[O:20][C:21]([CH3:27])([CH3:26])[C:22]([CH3:24])([CH3:25])[O:23]1

Participants

5

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 68315038HCID 68315038, compoundHCID 178418339Butyllithium

Product 1

HCID 68315186HCID 68315186, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by the general procedure described for compound 3, using 4-alkyl resorcinol dimethylether 2 0.104 g (0.5 mmol) in 4 ml of THF, n-BuLi 0.34 ml (0.55 mmol, 1.6 M solution in hexane) and PINBOP 0.15 ml (0.75 mmol). The product was obtained as a non-separable mixture 0.165 g of pinacol aryl boronate 4 and 4-alkyl resorcinol dimethylether 2 (in ratio 4:3 according to GC-MS analysis) and was used as it is in Suzuki coupling reaction. 1H NMR (300 MHz, CDCl3) δ ppm 6.28 (s, 2H), 3.76 (s, 6H), 2.55 (t, J=7.53 Hz, 2H), 1.55-1.63 (m, 2H), 1.27 (s, 6H), 1.26 (s, 6H), 1.24 (m, 4H), 0.87 (m, 3H). Exact mass calculated for C27H34O3 m/e 334.23. found 334.62.

Workup

  1. customThe title compound was prepared by the general procedure

Sources & evidence

ORD record
ord-2e7af5f2992347cc8756887b009eae7f
Source dataset
uspto-grants-2016_06
Patent number
US09365534B2

Reaction notes

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