Dimethyl malonate → HCID 66757258, compound

HRID 457358Notes

Reaction equation

HRID 457358 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-921d854e8cb245c3978d8b602ebc9ab7
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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