Methanol → HCID 5273039, compound

HRID 128756Notes

Reaction equation

HRID 128756 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([C:18]2[N:22]=[C:21](C(Cl)(Cl)Cl)[O:20][N:19]=2)[CH:15]=[C:14]([CH3:27])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1.[CH3:28][O-:29].[Na+].CO>CN(C)C=O.O>[CH3:1][C:2]1[CH:17]=[C:16]([C:18]2[N:22]=[C:21]([O:29][CH3:28])[O:20][N:19]=2)[CH:15]=[C:14]([CH3:27])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 9845603HCID 9845603, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 5273039HCID 5273039, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product of Example 12 (627 mg, 1.46 mmol) was added to a freshly prepared solution of sodium methoxide in methanol (1.5 equivalents sodium in 5 mL methanol) in dry dimethylformamide (3-5 mL) and the mixture was stirred at room temperature for 15-30 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate (3x). The combined organic extracts were washed with water, brine, dried (MgSO4) and concentrated in vacuo. The crude residue (0.64 g) was purified by chromatography (Silica Gel 60, first with 2% methanol in methylene chloride followed by 5% ethyl acetate in methylene chloride) to give pure title compound (308 rag) as a colorless oil which crystallized from methanol, mp 64.5°-65.5° C. (white solid).

Workup

  1. extractionextracted with ethyl acetate (3x)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue (0.64 g) was purified by chromatography (Silica Gel 60

Sources & evidence

ORD record
ord-749f61de508e4b7a98fe5e91808e00c1
Source dataset
uspto-grants-1995_11
Patent number
US05464848

Reaction notes

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