2,3-Dimethyl-2-butene → HCID 86725260, compound

HRID 576627Notes

Reaction equation

HRID 576627 reaction equation
[O:1]=[CH:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:7]2.CC(=C(C)C)C.O.P([O-])(O)(O)=[O:31].[Na+].Cl([O-])=O.[Na+]>C(O)(C)(C)C.C(OCC)(=O)C>[CH2:16]([O:15][C:13]([N:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([CH2:3][C:2]([OH:31])=[O:1])[CH:5]=2)[CH2:9]1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 112502,3-Dimethyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 86725259HCID 86725259, compound

Product 1

HCID 86725260HCID 86725260, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 5-(2-oxoethyl)isoindoline-2-carboxylate (290 mg, 1 mmol) in tert-butanol (10 mL) was added 2,3-dimethyl-but-2-ene (1.1 mL). To this mixture was added a solution comprising sodium dihydrogenphosphate hydrate (1.08 g, 8 mmol) and sodium chlorite (1.08 g, 9.5 mmol tech grade). This mixture was stirred for 20 min diluted with ethyl acetate, washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by silica chromatography (25 g silica eluted with 3-20% methanol in dichloromethane) to give the title compound as a white solid.

Workup

  1. washwashed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica chromatography (25 g silica eluted with 3-20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ab4556acd82f438f9234878411faef8d
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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