Hydrochloric Acid → 6-Iodoindane-5-carbaldehyde
Reaction equation
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[C:11]#N.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.Cl.CC[O:32]CC>ClCCl>[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[CH:11]=[O:32]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 6-iodoindane-5-carbonitrile (36.5 mg, 0.136 mmol) in dichloromethane (1.0 mL) under N2 at −78° C. was added a solution of 1N DIBALH in toluene (272 μL, 0.272 mmol) dropwise. The reaction was stirred at −78° C. for 15 min. Keeping the temperature at −78° C., another two portions of DIBALH (100 μL each) were added until the starting material disappeared by TLC. The reaction mixture was poured into 2N HCl (45 mL) and diluted with Et2O. The mixture was stirred for 0.5 h. The Et2O layer was separated. The aqueous layer was extracted with Et2O (2×). The organic extracts were combined, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, hexanes/EtOAc) to afford 6-iodoindane-5-carbaldehyde (27 mg, 73%). 1H NMR (500 MHz, CDCl3) δ 10.08 (s, 1H), 7.83 (s, 1H), 7.79 (s, 1H), 2.98 (t, J=7.5 Hz, 2H), 2.94 (t, J=7.5 Hz, 2H,), 2.19-2.13 (m, 2H).
Workup
- customat −78° C.
- stirringThe mixture was stirred for 0.5 h
- customThe Et2O layer was separated
- extractionThe aqueous layer was extracted with Et2O (2×)
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (Si, hexanes/EtOAc)
Sources & evidence
- ORD record
- ord-ef0778e71f4b412a90a9aa86fa742a19
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865707B2
Reaction notes
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