Potassium tert-butoxide → 8,10-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol

HRID 1513929Notes

Reaction equation

[OH:1][CH:2]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)[C:3]1[C:12]([C:13]2[C:18]([F:19])=[CH:17][C:16]([F:20])=[CH:15][C:14]=2F)=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([OH:22])=[CH:8]2.CC(C)([O-])C.[K+]>CN(C=O)C>[F:20][C:16]1[CH:15]=[C:14]2[C:13](=[C:18]([F:19])[CH:17]=1)[C:12]1[C:3](=[C:4]3[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:22])[CH:6]=[CH:5]3)[CH:2]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)=[CH:27][CH:28]=1)[O:1]2

Participants

Conditions

Temperature: 50 °C

Procedure

Alternatively, dissolve enantiomerically enriched 5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2,4,6-trifluoro-phenyl)-naphthalen-2-ol (804 mg, 1.59 mmol) in DMF (10 mL). Add potassium tert-butoxide (532 mg, 4.75 mmol). Heat at 50° C. for 2 minutes. Pour the reaction mixture into ice (5 g). Extract with ethyl acetate (100 mL). Separate the layers and wash the organic layer with 10% aqueous lithium chloride solution (20 mL×2). Dry with magnesium sulfate and concentrate in vacuo. Purify the residue over silica gel, eluting the material with a step gradient of methanol/dichloromethane (0 to 10%), to give the enantiomerically enriched title compound.

Workup

extractionExtract with ethyl acetate (100 mL)
customSeparate the layers
washwash the organic layer with 10% aqueous lithium chloride solution (20 mL×2)
dry with materialDry with magnesium sulfate
concentrationconcentrate in vacuo
customPurify the residue over silica gel
washeluting the material with a step gradient of methanol/dichloromethane (0 to 10%)

Sources & evidence

ORD record: ord-d74e021020df4d8fb255924f059a4c54
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217032B2

Reaction notes

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