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

HRID 1481349Notes

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 solution of BH3 (1.46 mL, 1M in THF) was added to a solution 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. solution 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 combined organic layers were dried over MgSO4 and concentrated 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 materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b9cf52ed3a6946028814895c958f8ac9
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409917B2

Reaction notes

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