Toluene → [2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-acetaldehyde

HRID 418925Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]#N.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.CC[O:38]CC>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][CH:17]=[O:38]

Participants

Reactant 4

HCID 1140Toluene

HCID 3283Diethyl Ether

HCID 21225700Diisobutylaluminumhydride

HCID 66652057[2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-acetonitrile

Product 1

HCID 72309410[2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-acetaldehydeYield 76%

Conditions

Temperature: -10 °C

Procedure

Dissolve [2-(2,5-dimethoxy-phenyl)-cyclopentyl]-acetonitrile (3.9 g, 16 mmol) in ether (85 ml), cool to −10° C., add diisobutylaluminum hydride 1.5M in toluene (19 ml, 29 mmol), and stir at −10° C. for 1 hour. Quench with 1N hydrochloric acid, and add ethyl acetate. Separate layers, wash organic with brine, dry, and concentrate to give the title compound (3 g, 76%): 1H NMR (CDCl3) δ 9.50-9.49 (m, 1H), 6.77-6.69 (m, 3H), 3.77 (s, 3H), 3.76 (s, 3H), 3.58-3.54 (m, 1H), 2.88-2.83 (m, 1H), 2.08-1.87 (m, 5H), 1.74-1.65 (m, 2H), 1.44-1.39 (m, 1H).

Workup

customQuench with 1N hydrochloric acid
additionadd ethyl acetate
washSeparate layers, wash organic with brine
customdry
concentrationconcentrate

Sources & evidence

ORD record: ord-f492e88fcd24404589544212df3f97eb
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093302B2

Reaction notes

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