Ethyl Acetate → (6-methoxy-2,3-dihydro-1H-inden-5-yl)boronic acid

HRID 985563Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[CH2:7][CH2:6][CH2:5]2.[Li]CCCC.[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C.CCOC(C)=O>C1COCC1>[CH3:12][O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][CH2:7]2)=[CH:3][C:2]=1[B:18]([OH:23])[OH:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.06 g (4.69 mmol) of 5-bromo-6-methoxyindane in 10 mL of THF was cooled to −78° C. and treated in a dropwise manner with 2.90 mL (4.64 mmol) of 1.6 M n-BuLi in hexanes. The mixture was stirred for 1 hr and was treated with 1.90 mL (8.2 mmol) of triisopropyl borate. The reaction was allowed to warm slowly to 0° C. and was stirred at this temperature for 0.5 hr. The reaction was quenched by the careful addition of 12 mL of aq 1N HCl. The layers were separated and the aqueous layer extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford 1.02 g. Flash chromatography (SiO2; 15% EtOAc in hexanes) gave 0.62 g (69%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.52 (s, 2H), 7.41 (s, 1H), 6.84 (s, 1H), 3.75 (s, 3H), 2.81 (t, J=7.3 Hz, 2H), 2.73 (t, J=7.3 Hz, 2H), 2.00-1.92 (m, 2H); IR (CHCl3) 3505 (br), 2945, 1612, 1570, 1487, 1465, 1417, 1297, 1252, 1161, 1129 cm−1; FDMS 192 (M+).

Workup

stirringwas stirred at this temperature for 0.5 hr
customThe reaction was quenched by the careful addition of 12 mL of aq 1N HCl
customThe layers were separated
extractionthe aqueous layer extracted with EtOAc (3×50 mL)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto afford 1.02 g

Sources & evidence

ORD record: ord-682f831641f940be864443ccbfc2bf10
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872743B2

Reaction notes

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