Tetrahydrofuran → HCID 10877241, compound

HRID 643894Notes

Reaction equation

HRID 643894 reaction equation
CO[C:3](=O)[C:4]([OH:9])(C)[CH2:5]C=C.[CH3:11][Mg+].[Br-].[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1>>[CH3:3][C:4]([OH:9])([C:16]([CH3:11])([OH:17])[CH2:15][CH:14]=[CH2:18])[CH3:5]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24978338Methyl 2-hydroxy-2-methylpent-4-enoateHCID 178418689HCID 178418689, compound

Product 1

HCID 10877241HCID 10877241, compound

Procedure

To a stirring solution of 2-hydroxy-2-methylpent-4-enoic acid methyl ester (1.12 g, 7.77 mmol) in THF (8 mL) at 0° C. is added MeMgBr (10 mL, 30 mmol) drop wise. The mixture is stirred for 3 h at room temperature and then quenched with sat. NH4Cl. It is then extracted with Et2O (3×50 mL). The organic layers are washed with water and brine, dried and concentrated to afford 2,3-dimethylhex-5-ene-2,3-diol.

Workup

  1. customquenched with sat. NH4Cl
  2. extractionIt is then extracted with Et2O (3×50 mL)
  3. washThe organic layers are washed with water and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-00d9f44322e3470cb38d5db96765547c
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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