Sodium Hydroxide → (R)-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol

HRID 2277390Notes

Reaction equation

[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].[CH3:24][C@@H:25]1[CH2:27][O:26]1>C1COCC1>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:24][C@H:25]([OH:26])[CH3:27])=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 30 °C

Procedure

To a suspension of 4-(4-nitrophenoxy)quinolin-7-ol (10 g, 35.5 mmol) in THF (35 mL)/aq. NaOH (37.8 g, 7.4%) was added (R)-2-methyloxirane (10.3 g, 177.3 mmol). The reaction was stirred at 30° C. for 18 hours then concentrated in vacuo. The mixture was diluted with EtOAc (50 mL). The organic phase was separated and concentrated in vacuo. The residue was purified by a column chromatography on silica gel (EtOAc/PE=1:1) to furnish the title compound as a yellow solid (3.6 g, 29.9%).

Workup

concentrationthen concentrated in vacuo
additionThe mixture was diluted with EtOAc (50 mL)
customThe organic phase was separated
concentrationconcentrated in vacuo
customThe residue was purified by a column chromatography on silica gel (EtOAc/PE=1:1)

Sources & evidence

ORD record: ord-dca25b11ee1d44b3983b5fc6da394755
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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