Dimethyl malonate → HCID 66757258, compound

HRID 1643192Notes

Reaction equation

HRID 1643192 reaction equation
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].Br[CH:13]([CH2:22][CH2:23][CH2:24][CH3:25])[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15]>CS(C)=O>[CH3:8][O:7][C:5](=[O:6])[CH:4]([CH:13]([C:14](=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:22][CH2:23][CH2:24][CH3:25])[C:3]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 10611006HCID 10611006, compound

Product 1

HCID 66757258HCID 66757258, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Small portions of NaH (60%, 7.92 g, 198 mmol) are added to a solution of dimethyl malonate (22.6 ml, 198 mmol) in DMSO (100 mL) at 0° C. The ice bath is removed and the mixture stirred at room temperature for 2 hours. The solution is rechilled to 0° C. and a solution of 2-bromo-1-phenyl-hexan-1-one (2-1) (16.8 g, 66 mmol) in DMSO (50 mL) is added slowly. The ice bath is removed and the mixture stirred overnight. Water (500 mL) is added and the mixture is extracted with EtOAc (4×150 mL). The combined extracts are washed with brine (300 mL), dried (Na2SO4), and evaporated, to provide the product as a light yellow oil. LC-MS (M+1) 307. 1H NMR (δ, CDCl3) 7.98-8.02 (m, 2H), 7.46-7.60 (m,3H), 4.18-4.28 (m, 1H), 4.03-4.12 (m, 1H), 3.80 (s, 3H), 3.6.1 (s, 3H), 1.55-1.63 (m, 2H), 1.02-1.20 (m, 4H), 0.76 (t, J=0.72 Hz, 3H).

Workup

  1. customThe ice bath is removed
  2. customis rechilled to 0° C.
  3. customThe ice bath is removed
  4. stirringthe mixture stirred overnight
  5. additionWater (500 mL) is added
  6. extractionthe mixture is extracted with EtOAc (4×150 mL)
  7. washThe combined extracts are washed with brine (300 mL)
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-2823937c14ab4715952e3513f5892dad
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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