Magnesium 2-methylpropan-2-olate → HCID 131727588, compound

HRID 2105262Notes

Reaction equation

HRID 2105262 reaction equation
[C:1]([SiH2:5][O:6][C:7]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8](=[CH:11][CH3:12])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C[C:26]([CH3:29])([O-:28])[CH3:27].[Mg+2].[CH3:31][C:32](C)([O-:34])[CH3:33].S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:47]([P:50](=O)(O)[OH:51])(C)C>CN(C=O)C>[CH:26]([O:28][P:50]([CH2:47][O:10][CH2:9][C:8]([C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[O:6][SiH2:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:11][CH3:12])(=[O:51])[O:34][CH:32]([CH3:33])[CH3:31])([CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 12040442Magnesium 2-methylpropan-2-olateHCID 86597089HCID 86597089, compoundHCID 131727589HCID 131727589, compound

Product 1

HCID 131727588HCID 131727588, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2-(tert-Butyl-diphenyl-silanyloxymethyl)-but-2-en-1-ol (see: J. Org. Chem. 58, 2151-2161, 1993), (660 mg (1.94 mmol)) in anhydrous DMF was added Magnesium t-butoxide 660 mg (3.88 mmol) followed by isopropylphosphonate tosylate 1.2 g (2.91 mmol). The reaction was stirred under Ar at 70° C. for 16 h, until the reaction was complete by TLC. Solvents were removed in vacuo and the residue (yellow gum) resuspended in EtOAc. Saturated NH4Cl— was added and the reaction extracted with EtOAc (2×40 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (gradient elution, hexanes/ethyl acetate, 9:1 to 2:3) yielded the title compound 674 mg (1.3 mmol; 67% yield).

Workup

  1. customSolvents were removed in vacuo
  2. additionSaturated NH4Cl— was added
  3. extractionthe reaction extracted with EtOAc (2×40 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washFlash chromatography (gradient elution, hexanes/ethyl acetate, 9:1 to 2:3)

Sources & evidence

ORD record
ord-00547ddadc7b4988a2c113bfb86f2e20
Source dataset
uspto-grants-2009_08
Patent number
US07579332B2

Reaction notes

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