Sodium Carbonate → HCID 15335307, compound

HRID 1721262Notes

Reaction equation

HRID 1721262 reaction equation
Br[CH2:2][C:3](=[N:8][OH:9])[C:4]([CH3:7])([CH3:6])[CH3:5].[CH2:10]([OH:14])[C:11](=[CH2:13])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:5][C:4]([C:3]1[CH2:2][CH2:12][C:11]([CH3:13])([CH2:10][OH:14])[O:9][N:8]=1)([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10557Methallyl alcoholHCID 85441254HCID 85441254, compound

Product 1

HCID 15335307HCID 15335307, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-bromo-3,3-dimethyl-2-butanone oxime (4.5 g) (J. Org. Chem., 1979, 44, 3861) in dichloromethane (150 mL) was added methallyl alcohol (22 mL) and sodium carbonate (16 g). The reaction mixture was stirred at room temperature for 40 h and then filtered through a pad of Celite. The solvent and excess alcohol were removed at reduced pressure. The residue was chromatographed on silica gel with 2:1 hexanes/ethyl acetate to give the title compound (3.2 g) as a low melting waxy solid. NMR (200 Mhz, CDCl3) 3.5 (m, 2H, CH2OH), 2.2-1.6 (m, 4H, ring CH2 's), 1.2 (s, 12H, t-Bu and Me). IR (Nujol) 3240 cm-1 (br, OH).

Workup

  1. filtrationfiltered through a pad of Celite
  2. customThe solvent and excess alcohol were removed at reduced pressure
  3. customThe residue was chromatographed on silica gel with 2:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-c9b7bcb6e633433d8ec0bb5b76f9864f
Source dataset
uspto-grants-1996_04
Patent number
US05510318

Reaction notes

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