Methanol → HCID 57706368, compound

HRID 1662386Notes

Reaction equation

HRID 1662386 reaction equation
[CH3:1][C:2]1([CH3:24])[C:6]([C:7]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][C:8]=2[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=2[F:23])=[CH:5][CH2:4][CH2:3]1.S(=O)(=O)(O)O.[CH3:30]O>>[CH3:1][C:2]1([CH3:24])[C:6]([C:7]2[CH:12]=[C:11]([C:13]([O:15][CH3:30])=[O:14])[CH:10]=[CH:9][C:8]=2[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=2[F:23])=[CH:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 57706354HCID 57706354, compound

Product 1

HCID 57706368HCID 57706368, compoundYield 98%

Procedure

To a flask containing 66.14A (75 mg, 230 μmol) in MeOH (2 mL) was added sulfuric acid (0.61 μL, 11 μmol), and the mixture was stirred at reflux overnight. The reaction was concentrated and then purified by silica gel chromatography (0 to 30% EtOAc/Hexanes) to provide 66.14B (77.0 mg, 98% yield).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction was concentrated
  3. custompurified by silica gel chromatography (0 to 30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-60bcdfa4f30342b9aeffc43c588145d1
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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