Acetic Acid → HCID 59590874, compound

HRID 2098978Notes

Reaction equation

HRID 2098978 reaction equation
[CH2:1]([C:3]1([CH2:13][C:14]([OH:16])=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH2:17](Cl)Cl.CO.C[Si](C=[N+]=[N-])(C)C.C(O)(=O)C>C(OCC)C>[CH2:1]([C:3]1([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 21226129Dichloromethane methanolHCID 59590777HCID 59590777, compound

Product 1

HCID 59590874HCID 59590874, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 25 mL conical flask was charged with 42.3 (0.11 g, 0.50 mmol) and 10:1 DCM/MeOH (5 mL). To the orange solution was added (trimethylsilyl)diazomethane (2.0 M solution in diethyl ether, commercially available from Aldrich) (0.30 mL, 0.60 mmol) dropwise (vigorous gas evolution). The resulting solution was stirred for 15 minutes at room temperature, quenched with acetic acid (0.029 mL, 0.50 mmol), and concentrated. The residue was purified by silica gel flash chromatography (0-30% EtOAc/hexanes) to afford 42.4 (0.104 g, 89% yield) as a yellow oil.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cce1f6378c074365a3e37705de3e1018
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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