Dimethylformamide → HCID 69004267, compound

HRID 2105746Notes

Reaction equation

HRID 2105746 reaction equation
[CH3:1][CH:2]([CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:13]=2)[CH:8]=1)[C:3]([OH:5])=O.O=S(Cl)Cl.CN(C=O)C.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][CH:2]1[C:3](=[O:5])[C:8]2=[C:9]3[C:14](=[CH:15][CH:16]=[C:7]2[CH2:6]1)[CH:13]=[CH:12][C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:10]3

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 69001798HCID 69001798, compound

Product 1

HCID 69004267HCID 69004267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-Methyl-3-(7-phenyl-2-naphthyl)propanoic acid (6.25 g, 21.5 mmole) was suspended in CH2Cl2 (20 ml), and SOCl2 (2.9 ml, 40 mmole) and 0.05 ml of DMF were added. The resulting mixture was stirred for 2 h at room temperature, refluxed for additional 1 h, evaporated and dried in vacuo. AlCl3 (4.3 g, 33 mmol) was suspended in CH2Cl2 (40 ml), and solution of obtained chloroanhydride in CH2Cl2 (20 ml) was added at 0° C. within 0.5 h. The resulting mixture was allowed to warm to room temperature, stirred for additional 2 h, and poured into ice/HCl (˜200 g+40 ml). The resulting mixture was extracted by CH2Cl2 (4×50 ml). Combined organic phase was washed by aq. KHCO3, dried over MgSO4, evaporated and dried in vacuo giving practically pure solid product. The yield 5.45 g (92%).

Workup

  1. temperaturerefluxed for additional 1 h
  2. customevaporated
  3. customdried in vacuo
  4. temperatureto warm to room temperature
  5. stirringstirred for additional 2 h
  6. extractionThe resulting mixture was extracted by CH2Cl2 (4×50 ml)
  7. washCombined organic phase was washed by aq. KHCO3
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. customdried in vacuo
  11. customgiving practically pure solid product

Sources & evidence

ORD record
ord-e89483cbf3d84a1b8e1a06c1ff5cb53f
Source dataset
uspto-grants-2009_08
Patent number
US07579417B2

Reaction notes

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