2-Methyl-2-butene → HCID 86701781, compound

HRID 2174135Notes

Reaction equation

HRID 2174135 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:20]([CH3:26])([CH2:23][CH:24]=[CH2:25])[CH:21]=[O:22])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]=[CH:6]2.CC(=CC)C.P([O-])(O)(O)=[O:33].[Na+].Cl([O-])=O.[Na+]>C(O)(C)(C)C.O.CCOC(C)=O>[C:16]([O:15][C:13]([N:8]1[C:9]2[C:5](=[C:4]([C:20]([CH3:26])([CH2:23][CH:24]=[CH2:25])[C:21]([OH:33])=[O:22])[C:3]([O:2][CH3:1])=[CH:11][C:10]=2[CH3:12])[CH:6]=[CH:7]1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86701782HCID 86701782, compound

Product 1

HCID 86701781HCID 86701781, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (±)-tert-butyl 5-methoxy-7-methyl-4-(2-methyl-1-oxopent-4-en-2-yl)-1H-indole-1-carboxylate (Example 156-C) (2 g, 5.60 mmol) in tert-butanol (37.3 mL) and water (18.65 mL) was added 2-methyl-2-butene (5.93 ml, 56.0 mmol), sodium dihydrogen phosphate (2.69 g, 22.38 mmol) and then sodium chlorite (2.53 g, 22.38 mmol). The reaction was allowed to stir at room temperature overnight for 17 hours. At this point the reaction was diluted with EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were dried over MgSO4 and concentrated to obtain the title compound that was use in the next step without further purification. MS (ESI+) m/z 374.3 (M+H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organics were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2b709848dc78447288d64946bfd1f960
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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