Sodium hydride → 6-bromo-2,2-di(but-3-en-1-yl)-2,3-dihydro-1H-inden-1-one

HRID 473019Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:15][CH2:16][CH:17]=[CH2:18]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]([CH2:4][CH2:3][CH:2]=[CH2:10])([CH2:15][CH2:16][CH:17]=[CH2:18])[C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 6-bromo-1-indanone (0.5330 g, 2.52 mmol) in dry THF (10 mL) was added NaH (0.3380 g, 60% in a mineral oil, 8.45 mmol) at 0° C. under nitrogen. After being stirred for 10 min, 4-iodobut-1-ene (1.3450 g, 7.39 mmol) was added and then the mixture was stirred at ambient temperature for 20 h. The reaction mixture was cooled to 0° C., quenched with 1 N HCl, extracted with ethyl acetate, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.1304 g of 6-bromo-2,2-di(but-3-en-1-yl)-2,3-dihydro-1H-inden-1-one. LC-MS tR=2.33 min in 3 min chromatography, m/z 319, 321 (MH+); 1H NMR (400 MHz, CDCl3) δ 7.84 (s, 1H), 7.67 (d, J=8 Hz, 1H), 7.33 (d, J=8 Hz, 1H), 5.76-5.66 (m, 2H), 4.94-4.87 (m, 4H), 2.98 (s, 2H), 1.98-1.63 (m, 8H); 13C NMR (100 MHz, CDCl3) δ 209.23, 151.43, 138.85, 137.85, 137.54, 127.94, 126.75, 121.55, 114.81, 52.87, 37.28, 36.58, 28.54.

Workup

stirringthe mixture was stirred at ambient temperature for 20 h
customquenched with 1 N HCl
extractionextracted with ethyl acetate
dry with materialdried over Na2SO4
customAfter the solvents were evaporated
customthe residue was purified by chromatography on silica gel
washeluted with hexanes/ethyl acetate

Sources & evidence

ORD record: ord-083d66eeb3d54c108354df9dff6f0009
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633212B2

Reaction notes

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