2-Methyl-2-butene → HCID 89662789, compound

HRID 1479035Notes

Reaction equation

HRID 1479035 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].CC(=CC)C.[C:16]([Si:20]([CH3:35])([CH3:34])[O:21][CH2:22][CH:23]([CH3:33])[O:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=[O:28])([CH3:19])([CH3:18])[CH3:17]>O.O1CCOCC1>[C:16]([Si:20]([CH3:35])([CH3:34])[O:21][CH2:22][CH:23]([CH3:33])[O:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[C:27]([OH:6])=[O:28])([CH3:18])([CH3:19])[CH3:17]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 89651613HCID 89651613, compound

Product 1

HCID 89662789HCID 89662789, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium chlorite (1.17 g; 12.9 mmol; 5.5 eq.) and sodium dihydrogenphosphate (1.01 g; 8.44 mmol; 3.6 eq.) in water (10 mL) was added dropwise to a mixture of 2-methyl-2-butene (2 mL) and 2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethoxy]-benzaldehyde (690 mg; 2.34 mmol; 1 eq.) in 1,4-dioxane (10 mL). The reaction mixture was stirred at room temperature for 1.5 hour. After dilution with EA, the solution was washed with 1M HCl, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (690 mg, 95%) as a white solid. UPLC/MS: (MS−) 309.1 ([M−H]−).

Workup

  1. washAfter dilution with EA, the solution was washed with 1M HCl
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39764a0a6610442c87f66924a7c9befc
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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