Barium hydroxide → N-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]-2-aminoethanol

HRID 1023985Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:28]=[C:27]([CH2:29][CH3:30])[CH:26]=[CH:25][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH2:21][O:20]C2=O)=[CH:14][C:13]=1[F:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Ba+2].[OH-]>CO.O>[CH2:1]([O:8][C:9]1[CH:28]=[C:27]([CH2:29][CH3:30])[CH:26]=[CH:25][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:22][CH2:21][OH:20])=[CH:14][C:13]=1[F:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 3-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]oxazolidin-2-one (350 mg, 0.85 mmol) in 5 ml of methanol was added barium hydroxide (245 mg, 1.28 mmol) taken in 5 ml of water. The reaction mixture was warmed to 65° C. and stirred overnight (reaction was complete on TLC). The reaction mixture concentrated in vacuo to remove methanol, diluted with water and the aqueous layer was extracted with ethyl acetate. The combined organic fraction was washed with brine, dried over anhydrous Na2SO4 and concentrated to get 300 mg, 91.57% of the title compound as a brown oil, used as such in the next step.

Workup

custom(reaction was complete on TLC)
concentrationThe reaction mixture concentrated in vacuo
customto remove methanol
additiondiluted with water
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic fraction was washed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-3c59ef4dec25467ea4c7eded8abf63d0
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722746B2

Reaction notes

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