Cornforth reagent → HCID 18786304, compound

HRID 357242Notes

Reaction equation

HRID 357242 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][C:26]([OH:35])([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)[CH:10]([CH2:12][O:13][Si:14]([CH3:20])([CH3:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[OH:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][C:26]([OH:35])([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:27][CH2:28]2)[C:10](=[O:11])[CH2:12][O:13][Si:14]([CH3:20])([CH3:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 18936603HCID 18936603, compound

Product 1

HCID 18786304HCID 18786304, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of the alcohol from Step 1 (21.5 g, 39.8 mmol) in CH2Cl2 (600 mL) with PDC (22.5 g, 59.9 mmol). Stir the resulting black mixture for 12 h. Filter the reaction mixture through a plug of celite and wash plug with CH2Cl2 (200 mL) and EtOAc (200 mL). Concentrate the filtrate under reduced pressure to give the crude product as a black oil. Purify by silica gel chromatography (column: 10 cm ×24 cm; pack column in CH2Cl2 and elute using a gradient of 100% CH2 Cl2 to 5% CH3OH(NH3)/CH2Cl2) to obtain 16 g (29.9 mmol, 75%) of the title compound as a tan foam.

Workup

  1. filtrationFilter the reaction mixture through a plug of celite
  2. washwash plug with CH2Cl2 (200 mL) and EtOAc (200 mL)
  3. concentrationConcentrate the filtrate under reduced pressure
  4. customto give the crude product as a black oil
  5. customPurify by silica gel chromatography (column
  6. washpack column in CH2Cl2 and elute

Sources & evidence

ORD record
ord-e7a9faf233ad49e2b04d69b9b11e7e9b
Source dataset
uspto-grants-1998_11
Patent number
US05840725

Reaction notes

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