Water → 8-Fluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol

HRID 1513948Notes

Reaction equation

HRID 1513948 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH:20]([OH:36])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:23][CH:22]=2)=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]2.[H-].[Na+].O>CN(C=O)C>[F:8][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:7]=1)[C:9]1[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]3)[CH:20]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)=[CH:25][CH:26]=1)[O:36]2

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 670047256-(2,4-Difluoro-phenyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-ol

Product 1

HCID 112135468-Fluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-olYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 6-(2,4-difluoro-phenyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-ol (3.4 g, 7.0 mmol) in dry DMF (70 mL). Slowly add sodium hydride (440 mg, 18 mmol) and plunge into a 140° C. oil bath for 30 minutes. Cool to room temperature and pour into water. Adjust the pH to 7 and extract three times with methylene chloride. Wash combined organic layers with water, dry with sodium sulfate, filter and concentrate. Triturate with ether to yield 2.2 g (69%) of the title compound: mass spectrum (ion spray) m/z=470.3 (M+H).

Workup

  1. extractionextract three times with methylene chloride
  2. washWash
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customTriturate with ether

Sources & evidence

ORD record
ord-1540b9f9ec9c4b3db769ed2bf930bffd
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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