Ethanol → HCID 23143862, compound

HRID 1985822Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[O:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[CH2:7]([O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][C:16]=1[O:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Lithium aluminium hydride (2.6 g) was suspended in tetrahydrofuran (30 mL), and to the mixture was added dropwise a solution of 4-benzyloxy-3-(4-benzyloxybutoxy)benzonitrile (5.9 g) in tetrahydrofuran (30 mL) under ice-cooling. The mixture was stirred at 60° C. for 2 hours. After the mixture was cooled in an ice bath, ethanol and water were successively added dropwise to the reaction mixture. To the reaction mixture was added anhydrous sodium sulfate, and the insoluble material was removed by filtration through celite. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (2.5 g).

Workup

temperaturecooling
temperatureAfter the mixture was cooled in an ice bath
customthe insoluble material was removed by filtration through celite
concentrationThe filtrate was concentrated under reduced pressure
customthe obtained residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record: ord-54fe7b87f4f94c49af7508509018f511
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547680B2

Reaction notes

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