Water → HCID 131732692, compound

HRID 1466467Notes

Reaction equation

HRID 1466467 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.COC1C=CC(C[O:22][CH:23]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[C@@H:36]([CH2:46][CH2:47][CH2:48][C:49]4[S:53][C:52]([C:54]([O:56][CH3:57])=[O:55])=[CH:51][CH:50]=4)[CH2:37][CH2:38][C:39]=3[C:40]#[C:41][Si:42]([CH3:45])([CH3:44])[CH3:43])=[CH:31][CH:30]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=CC=1.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:22][CH:23]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[C@@H:36]([CH2:46][CH2:47][CH2:48][C:49]3[S:53][C:52]([C:54]([O:56][CH3:57])=[O:55])=[CH:51][CH:50]=3)[CH2:37][CH2:38][C:39]=2[C:40]#[C:41][Si:42]([CH3:43])([CH3:44])[CH3:45])=[CH:31][CH:30]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 131732693HCID 131732693, compound

Product 1

HCID 131732692HCID 131732692, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DDQ (160 mg, 0.71 mmol) was added to a solution of 1-2 (392 mg, 0.61 mmol) and H2O (0.9 mL) in CH2Cl2 (18 mL). After 30 minutes, saturated NaHCO3 solution (40 mL) was added and the resulting mixture was extracted with CH2Cl2 (3×25 mL). The combined CH2Cl2 solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography using a Combiflash unit from Teledyne Isco (0% ethyl acetate/hexanes→40%) to give the title compound (66 mg, 21%).

Workup

  1. extractionthe resulting mixture was extracted with CH2Cl2 (3×25 mL)
  2. washThe combined CH2Cl2 solution was washed with brine
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c72ad4282b814709917f25d631398d2c
Source dataset
uspto-grants-2015_04
Patent number
US09000032B2

Reaction notes

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