Dimethylformamide dimethyl acetal → HCID 66846726, compound

HRID 1466640Notes

Reaction equation

HRID 1466640 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH:17]2[CH2:19][CH2:18]2)=[C:6]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1.[CH3:20][N:21]([CH:23](OC)OC)[CH3:22]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH:17]2[CH2:19][CH2:18]2)=[C:6]([CH:7]=1)[C:8]([C:9](=[CH:20][N:21]([CH3:23])[CH3:22])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:15]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 66846757HCID 66846757, compound

Product 1

HCID 66846726HCID 66846726, compound

Procedure

Ethyl 3-(5-chloro-2-cyclopropoxyphenyl)-3-oxopropanoate (21.8 g, 77 mmol) was dissolved in 150 mL of DMF-DMA. The mixture was heated to reflux for 2 hours. Evaporation gave a yellow solid which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ: 7.69 (s, 1H), 7.39 (s, 1H), 7.29 (dd, J=2.4, 8.8 Hz, 1H), 7.15 (d, J=8.8 Hz, 1H), 3.92 (q, J=6.8 Hz, 2H), 3.69-3.65 (m, 1H), 3.10 (br, 6H), 0.88 (t, J=6.8 Hz, 3H), 0.77-0.71 (m, 4H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customEvaporation
  4. customgave a yellow solid which
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-83fa6439ff4c424b904420b25f0fb38b
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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