1,1-Dichloroethane → HCID 86607648, compound

HRID 1593647Notes

Reaction equation

HRID 1593647 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[C:6]([N+:13]([O-:15])=[O:14])=[CH:5]2.C[CH2:17][O:18][C:19]([CH3:21])=O.Cl[CH:23](Cl)[CH3:24]>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[C@@:6]1([N+:13]([O-:15])=[O:14])[CH2:23][CH:24]=[C:19]([O:18][CH3:17])[CH2:21][C@@H:5]21

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 8857Ethyl AcetateHCID 20136729HCID 20136729, compound

Product 1

HCID 86607648HCID 86607648, compoundYield 63%

Procedure

6-fluoro-3-nitro-2H-chromen-2-one (8.50 g, 40.66 mmol) and 2,2-dimethoxy-1-butene (10.2 g, 120 mmol) were stirred together in dichloroethane (100 mL) at reflux under a N2 atmosphere for 1 h. TLC (25% EtOAc in hexanes) indicated reaction was complete, so reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The resulting brown solid was purified by flash chromatography on silica gel to afford the title compound as an off-white solid (7.50 g, 63%); MS (APPI) m/z=294 [M+H]+.

Workup

  1. temperatureat reflux under a N2 atmosphere for 1 h
  2. customreaction
  3. customwas complete, so reaction mixture
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting brown solid was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f0f18c903b2f45ad8942feaf8b0435e3
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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