Ethylene Glycol → HCID 58923385, compound

HRID 1951056Notes

Reaction equation

HRID 1951056 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[C:11]1[C:10]([OH:17])=[CH:9][C:8]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:7][C:6]=1[O:5]2.[CH2:24]([OH:27])[CH2:25][OH:26].[H-].[Na+]>CN(C=O)C>[OH:17][C:10]1[C:11]2[C:12](=[O:16])[C:13]3[C:4](=[CH:3][C:2]([O:26][CH2:25][CH2:24][OH:27])=[CH:15][CH:14]=3)[O:5][C:6]=2[CH:7]=[C:8]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 11209251HCID 11209251, compound

Product 1

HCID 58923385HCID 58923385, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-fluoro-1-hydroxy-3-morpholin-4-yl-xanthen-9-one (30.0 mg, 0.095 mmol) and ethylene glycol (59.1 mg, 0.951 mmol) in anhydrous DMF (1 mL) was treated with NaH (40.0 mg, 0.951 mmol). The bubbling reaction was stirred for 15 minutes at room temperature, then heated at 80° C. for 1 hour. The reaction mixture was quenched with water and extracted with EtOAc (3×50 mL). The combined organics were washed with water (3×15 mL), dried (MgSO4), and concentrated to produce an oil. The oil was purified via Biotage chromatography using a gradient of 2.5%-5% MeOH/CH2Cl2 as eluent to yield 12 mg (35%) of 1-hydroxy-6-(2-hydroxyethoxy)-3-morpholin-4-yl-xanthen-9-one as a white powder. Rf=0.55 (5% MeOH/CH2Cl2). 1H NMR (DMSO-d6, 400 MHz) δ: 12.91 (s, 1H), 8.05 (d, 1H), 7.10 (m, 2H), 6.48 (s, 1H), 6.34 (s, 1H), 4.98 (m, 1H), 4.18 (t, 2H), 3.78 (t, 2H), 3.70 (m, 4H), 3.38 (m, 4H). LRMS (APCI, positive): Da/e 358.4 (m+1).

Workup

  1. customThe bubbling reaction
  2. temperatureheated at 80° C. for 1 hour
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined organics were washed with water (3×15 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto produce an oil
  9. customThe oil was purified via Biotage chromatography

Sources & evidence

ORD record
ord-5ebad421ecfc4fd3bbe2be75d3eff5b3
Source dataset
uspto-grants-2013_03
Patent number
US08404681B2

Reaction notes

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