2-Methoxyethanol → HCID 136389467, compound

HRID 2378064Notes

Reaction equation

HRID 2378064 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:11]([C:19]3([C:22]([OH:24])=[O:23])[CH2:21][CH2:20]3)[O:10][N:9]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:29][O:30][CH2:31][CH2:32]O>C(OCC)(=O)C>[CH3:29][O:30][CH2:31][CH2:32][O:23][C:22]([C:19]1([C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:21][CH2:20]1)=[O:24]

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 24386Thionyl ChlorideHCID 136078238HCID 136078238, compound

Product 1

HCID 136389467HCID 136389467, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution consisting of the product of Example 87 (0.50 g) in 2-methoxyethanol (5 mL) is added thionyl chloride (1.0 mL.) The mixture is heated to 60° C. for 18 h is and is subsequently cooled, diluted with ethyl acetate, washed with water and brine solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with a gradient (0 to 50% ethyl acetate in hexanes) afforded the title compound (0.37 g); MS (APCI+) m/z 380 (MH+.)

Workup

  1. temperatureis subsequently cooled
  2. washwashed with water and brine solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate is purified by flash silica gel column chromatography
  6. washElution with a gradient (0 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5d25388a17584d4c912c4d5dfd5bbe74
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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