Tetrahydrofuran → [2-[4-(Tetradecyloxy)phenyl]ethyl]aminobenzenemethanol

HRID 484616Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]([CH:40]=[CH:41][CH:42]=2)C(OCC)=O)=O)=[CH:24][CH:23]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[O:43]1CCC[CH2:44]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC.C(OCC)(=O)C>[CH2:7]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][NH:31][C:32]2[CH:42]=[CH:41][CH:40]=[CH:34][C:33]=2[CH2:44][OH:43])=[CH:26][CH:27]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 42.36 ml of 1 molar lithium aluminum hydride in either is added dropwise under argon over 20 minutes a solution of ethyl 3-[[[4-(tetradecyloxy)phenyl]acetyl]amino]benzoate in 50 ml of either and 50 ml of tetrahydrofuran. The mixture is refluxed for 3 hours, cooled to 0° C. and ethyl acetate added. Saturated sodium sulfate is added followed by ether. The mixture is filtered and the cake washed with ether. The filtrate is evaporated and the residue chromatographed on silica gel using 9:1 chloroform:ethyl acetate. The product fractions are combined and evaporated to a residue which is crystallized from hexane to give 4.5 g of the desired product as a white solid, m.p. 67°-70° C.

Workup

temperatureThe mixture is refluxed for 3 hours
filtrationThe mixture is filtered
washthe cake washed with ether
customThe filtrate is evaporated
customthe residue chromatographed on silica gel using 9:1 chloroform
customevaporated to a residue which
customis crystallized from hexane

Sources & evidence

ORD record: ord-ee09bea64a054d299e44e9da5f60ae67
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05231182

Reaction notes

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