Sodium Hydroxide → 2-((2-(Aminomethyl)-3,5-dichlorobenzyl)oxy)ethanol

HRID 1051952Notes

Reaction equation

C([O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[C:10]=1[C:17]#[N:18])(=O)C.[OH-].[Na+]>C1COCC1.CO>[NH2:18][CH2:17][C:10]1[C:11]([Cl:16])=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[CH2:8][O:7][CH2:6][CH2:5][OH:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A soln. of BH3 (1.46 mL, 1M in THF) was added to a soln. of 2-((3,5-dichloro-2-cyanobenzyl)oxy)ethyl acetate (0.36 mmol) in 1.5 mL MeOH. The reaction mixture was heated to 60° C. for 3 h. At 0° C., 1.5 mL MeOH was dropwise added and the mixture was stirred until gaz evolution was finished. An aq. soln. of 10% NaOH was added still under cooling. The solvent was removed under vacuo, the residue was diluted with water and extracted 3 times with EtOAc. The comb. org. layers were dried over MgSO4 and conc. in vacuo to give the desired product as yellow solid.

Workup

temperatureunder cooling
customThe solvent was removed under vacuo
additionthe residue was diluted with water
extractionextracted 3 times with EtOAc
dry with materiallayers were dried over MgSO4 and conc. in vacuo

Sources & evidence

ORD record: ord-12ff7c21031a4b8dafcd7f9203266c22
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388197B2

Reaction notes

Loading…