Water → HCID 131727557, compound

HRID 2099887Notes

Reaction equation

HRID 2099887 reaction equation
[C:1]([SiH2:5][O:6][C:7]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:8]12[CH:23]([O:24]CC3C=CC4C(=CC=CC=4)C=3)[CH:12]([CH:13]([N:15]3[CH:20]=[CH:19][C:18](=[O:21])[NH:17][C:16]3=[O:22])[O:14]1)[O:11][N:10]([CH3:36])[CH2:9]2)([CH3:4])([CH3:3])[CH3:2].O.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[C:1]([SiH2:5][O:6][C:7]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:8]12[CH:23]([OH:24])[CH:12]([CH:13]([N:15]3[CH:20]=[CH:19][C:18](=[O:21])[NH:17][C:16]3=[O:22])[O:14]1)[O:11][N:10]([CH3:36])[CH2:9]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178479974HCID 178479974, compound

Product 1

HCID 131727557HCID 131727557, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 53 (1 mmol) in anhydrous CH2Cl2 (10 mL) was added water (0.8 mL) and the biphasic solution was stirred for 5 minutes. To this solution is added DDQ (2.2 mmol). The reaction mixture was stirred for 8 hours when the reaction was complete. It was diluted with CH2Cl2 (100 mL) and washed with 2% sodium bisufite solution. The aqueous layer was extracted until all the compound was in organic layer. The organic layer was washed with saturated bicarbonate followed by brine then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the product was purified on silica gel to give compound 54 in nearly quantitative yield.

Workup

  1. stirringThe reaction mixture was stirred for 8 hours when the reaction
  2. washwashed with 2% sodium bisufite solution
  3. extractionThe aqueous layer was extracted until all the compound
  4. washThe organic layer was washed with saturated bicarbonate
  5. dry with materialthen dried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe product was purified on silica gel

Sources & evidence

ORD record
ord-e9f5c82643f8431c8130ed4facea60b8
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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