3-Methyl-2-butanone → 2-(4-Iodophenyl)-3-methylbutan-2-ol

HRID 1025802Notes

Reaction equation

C([Li])CCC.I[C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][CH:8]=1.[CH3:14][CH:15]([CH3:19])[C:16](=[O:18])[CH3:17]>C1COCC1>[I:13][C:10]1[CH:11]=[CH:12][C:7]([C:16]([OH:18])([CH:15]([CH3:19])[CH3:14])[CH3:17])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyl lithium (139 mL of a 2M solution in hexanes, 277 mmol) was added via canula to a stirred solution 1,4-diiodobenzene (89.0 g, 277 mmol) in THF (500 mL) at −78° C. such that the internal temperature was maintained below −65° C. during the addition process. After 0.5 h, 3-methyl-2 butanone (24.0 g, 280 mmole) was added via syringe, again maintaining the internal temperature below −65° C. After 0.5 h, the reaction mixture was warmed to 0° C. and quenched with saturated aqueous ammonium chloride. The resulting mixture was dried (MgSO4), concentrated in vacuo, and the crude residue purified by flash chromatography on silica gel (gradient elution; 10-25% EtOAc/hexanes) to afford the title compound 5a. 1H NMR (500 MHz, CDCl3) δ 7.67 (d, 2H, J=7.5 Hz), 7.20 (d, 2H, J=7.5 Hz), 3.79 (s, 1H), 2.00 (m, 1H, J=7.0 Hz), 1.52 (s, 3H), 0.92 (d, 3H, J=7.0 Hz), 0.81 (d, 3H, J=7.0 Hz).

Workup

temperaturewas maintained below −65° C. during the addition process
temperatureagain maintaining the internal temperature below −65° C
waitAfter 0.5 h
customquenched with saturated aqueous ammonium chloride
dry with materialThe resulting mixture was dried (MgSO4)
concentrationconcentrated in vacuo
customthe crude residue purified by flash chromatography on silica gel (gradient elution; 10-25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-b1ae7c3075734af28706180c388dc970
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729104B2

Reaction notes

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