2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 53752512, compound

HRID 863108Notes

Reaction equation

HRID 863108 reaction equation
[O:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[CH:16]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:11][CH:10]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.OS([O-])=O.[Na+].CCOC(C)=O>C(Cl)Cl>[O:1]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[C:16]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:13][CH:14]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 23665763Sodium BisulfiteHCID 67643887HCID 67643887, compound

Product 1

HCID 53752512HCID 53752512, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl (2RS,3SR)-3-(4-t-butyldimethylsiloxyphenyl)-1-oxoindane-2-carboxylate (130 mg, 0.32 mmol) in CH2Cl2 (3 ml) under an argon atmosphere was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (80 mg, 0.35 mmol). The resulting mixture was stirred for 2.5 h. Aqueous NaHSO3 and EtOAc were added, and the mixture was stirred for 5 min. The aqueous phase was separated and extracted with EtOAc, and the combined organic extracts were washed successively with aqueous NaHCO3, H2O and saturated aqueous NaCl and dried. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel to afford the title compound (110 mg, 85%).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. customThe aqueous phase was separated
  3. extractionextracted with EtOAc
  4. washthe combined organic extracts were washed successively with aqueous NaHCO3, H2O and saturated aqueous NaCl
  5. customdried
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-5e0f0f2dd4454a428d3036b832e95084
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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