2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86600897, compound

HRID 2110346Notes

Reaction equation

HRID 2110346 reaction equation
[N:1]1([CH:10]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH:11]([OH:16])[C:12]([O:14][CH3:15])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[OH:16][CH:11]([CH:10]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86600898HCID 86600898, compound

Product 1

HCID 86600897HCID 86600897, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of methyl (2SR,3SR)-3-(2,3-dihydro-1H-indol-1-yl)-2-hydroxy-3-(4-methoxyphenyl)propanoate (2.63 g, 8.0 mmol) in anhydrous toluene (50 mL) at 0° C. under nitrogen was added a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.87 g, 8.2 mmol) in anhydrous toluene (50 mL) over 5 minutes. The reaction mixture was stirred 0° C. to room temperature for 1.5 hours then quenched by the addition of 7% w/v aqueous sodium carbonate solution (100 mL). The resulting biphasic mixture was stirred vigorously for 5 minutes then partitioned between ethyl acetate (300 mL) and 7% w/v aqueous sodium carbonate (250 mL). The organic phase was separated, washed with 7% w/v aqueous sodium carbonate solution (3×250 mL), water (250 mL) and saturated brine (250 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a lilac solid. Purification by flash chromatography (silica, 20%, 30% ethyl acetate/hexane) afforded 2.5 g (96%) of methyl (2SR,3SR)-2-hydroxy-3-(1H-indol-1-yl)-3-(4-methoxyphenyl)propanoate as a cream solid. MS (ES) m/z 326.3 ([M+H]+); HRMS: calcd for C19H19NO4+H+, 326.13869; found (ESI, [M+H]+), 326.1378.

Workup

  1. customthen quenched by the addition of 7%
  2. stirringThe resulting biphasic mixture was stirred vigorously for 5 minutes
  3. customthen partitioned between ethyl acetate (300 mL) and 7%
  4. customThe organic phase was separated
  5. washwashed with 7% w/v aqueous sodium carbonate solution (3×250 mL), water (250 mL) and saturated brine (250 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a lilac solid
  10. customPurification by flash chromatography (silica, 20%, 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cd9ed683ff4b4ddcb77f79e1807a6b61
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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