Diethyl Ether → 2-(3-Fluoro-4-methoxyphenyl)ethanamine

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[F:12][C:13]1[CH:18]=[C:17]([CH:19]=[CH:20][N+:21]([O-])=O)[CH:16]=[CH:15][C:14]=1[O:24][CH3:25]>C(OCC)(=O)C>[F:12][C:13]1[CH:18]=[C:17]([CH2:19][CH2:20][NH2:21])[CH:16]=[CH:15][C:14]=1[O:24][CH3:25]

Participants

Procedure

Lithium aluminum hydride (200 mL of 1 M in diethyl ether) was placed in a 1 L round bottomed flask along with 300 mL of diethyl ether. Intermediate 81 was placed in the thimble of a soxhlet extractor atop this flask and the mixture refluxed for 24 hours. The mixture was cooled to ° 0 C and 50 mL of ethyl acetate added dropwise. After stirring for 1 hour, the mixture was quenched with 100 mL of 1 N KHSO4. The Organic layer was separated washed with sat. NaHCO3, sat. NaCl, and dried over MgSO4. Removal of the solvent gave product. LC-MS showed the product had the expected M+H+ of 170. It was used in the next step without purification.