Dimethylformamide dimethyl acetal → HCID 53889968, compound

HRID 526398Notes

Reaction equation

HRID 526398 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[CH3:16][N:17]([CH3:19])[CH:18]=[C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 90266Methyl 4-methoxyphenylacetate

Product 1

HCID 53889968HCID 53889968, compoundYield 6.91%

Procedure

Combined methyl 2-(4-methoxyphenyl)acetate (3.58 mL, 22.20 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (11.89 mL, 89 mmol) and heated to 100° C. for 14 h. The reaction was concentrated in vacuo to afford a light yellow oil which was purified by flash chromatography (100 g basic silica using a 5% to 50% EtOAc in heptanes gradient to give the title compound (361 mg, 6.91%) as a colorless oil. MS m/z [M+H]+ 236.1.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto afford a light yellow oil which
  3. customwas purified by flash chromatography (100 g basic silica using a 5% to 50% EtOAc in heptanes gradient

Sources & evidence

ORD record
ord-68474e6658994452a56db432de4d4adb
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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