4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → (E)-N,N-dimethyl-1-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)methanamine

HRID 1466303Notizen

Reaktionsgleichung

[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][BH:4][O:3]1.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=1)#[CH:11]>C1(C)C=CC=CC=1>[CH3:20][N:19]([CH3:21])[CH2:18][C:15]1[CH:16]=[CH:17][C:12](/[CH:10]=[CH:11]/[B:4]2[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:9])([CH3:1])[O:3]2)=[CH:13][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (1.20 mL, 8.23 mmol) was added to an argon-purged solution of 1-(4-ethynylphenyl)-N,N-dimethylmethanamine (262 mg, 1.65 mmol) and HRuCl(CO)(PPh3)3 (104.1 mg, 0.11 mmol) in toluene (9.0 mL). The resulting mixture was heated at 50° C. for 12 h. The product was extracted into Et2O (250 mL), and the organic layer was washed sequentially with water (3×20 mL) and brine (20 mL), dried (Na2SO4) and evaporated in vacuo. Purification by column chromatography (silica gel, 50-100% CH2Cl2 in Et2O) gave (E)-N,N-dimethyl-1-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)methanamine (402 mg, containing 20% pinacol impurity by 1H NMR, 68% yield). 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=8 Hz, 2H), 7.4 (d, 1H), 7.28 (d, 2H), 6.16 (d, 1H), 3.42 (s, 2H), 2.24 (s, 6H), 1.32 (s, 12H); MS ESI 288.0 [M+H]+, calcd for [C17H26BNO2+H]+ 288.2.

Aufarbeitung

extractionThe product was extracted into Et2O (250 mL)
washthe organic layer was washed sequentially with water (3×20 mL) and brine (20 mL)
dry with materialdried (Na2SO4)
customevaporated in vacuo
customPurification by column chromatography (silica gel, 50-100% CH2Cl2 in Et2O)

Quellen und Nachweise

ORD-Eintrag: ord-2e25752c957a47f5afc7ac404cca693b
Quelldatensatz: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08999968B2

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