2-Methyl-2-butene → HCID 66658660, compound

HRID 420818Notes

Reaction equation

HRID 420818 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[O:18])=[C:9]1[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.[OH:27]P([O-])(O)=O.[K+].Cl([O-])=O.[Na+]>C(#N)C.C(O)(C)(C)C.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([OH:27])=[O:18])=[C:9]1[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-butene2×HCID 516951Monobasic potassium phosphate3×HCID 23668197Sodium Chlorite3×HCID 86615523HCID 86615523, compound2×

Product 1

HCID 66658660HCID 66658660, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

To a suspension of 1-benzyl-2-isopropyl-1H-indole-3-carbaldehyde (Compound 40, 545 mg, 2.0 mmol) in acetonitrile (6 ml), tert-butanol (6 ml) and H2O (12 ml) was added 2-methyl-2-butene (8 ml), potassium phosphate monobasic (5.4 g, 40 mmol), sodium chlorite (80%, 2.3 g, 40 mmol). The mixture was stirred at room temperature for 16 h, more potassium phosphate monobasic (5.4 g, 40 mmol) and sodium chlorite (80%, 2.3 g, 40 mmol) were added and the mixture was stirred at room temperature for an additional 24 h, at which time more potassium phosphate monobasic (5.4 g, 40 mmol), sodium chlorite (80%, 2.3 g, 40 mmol), H2O (8 ml), and 2-methyl-2-butene (8 ml) were added and the mixture was stirred for another 48 h. The solvent was removed in vacuo and the residual solid was washed with CHCl3 (×3) and filtered. The filtrate was concentrated and was purified by flash chromatography on silica gel eluting with 0-20% EtOAc-hexanes to yield 1-benzyl-2-isopropyl-1H-indole-3-carboxylic acid (Compound 41) as a yellow solid.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for another 48 h
  3. customThe solvent was removed in vacuo
  4. washthe residual solid was washed with CHCl3 (×3)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customwas purified by flash chromatography on silica gel eluting with 0-20% EtOAc-hexanes

Sources & evidence

ORD record
ord-24fd01e060884a9db229069d5cd5cb03
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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