Methanol → HCID 57706395, compound

HRID 1662506Notes

Reaction equation

HRID 1662506 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([CH2:14][CH3:15])[CH2:10][C:11]([OH:13])=[O:12].[CH3:16]O.S(=O)(=O)(O)O>CCOCC>[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([CH2:14][CH3:15])[CH2:10][C:11]([O:13][CH3:16])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 57707129HCID 57707129, compound

Product 1

HCID 57706395HCID 57706395, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A 500 mL round bottom flask was charged with 77.E (21.5 g, 101 mmol), MeOH (300 mL), and sulfuric acid (1.08 mL, 20.3 mmol). The solution was stirred for 1 hour at 80° C., cooled to room temperature, and diluted with ether. The organic layers were washed with saturated aqueous NaHCO3, water, and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-30% EtOAc/hexane) to afford 77.F (20.6 g, 90% yield) as a yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layers were washed with saturated aqueous NaHCO3, water, and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel flash chromatography (0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-332b5d410305458f882e039df7302624
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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