Water → HCID 66756925, compound

HRID 1643193Notes

Reaction equation

HRID 1643193 reaction equation
O.[Na+].[Cl-].[CH3:4][O:5][C:6](=[O:25])[CH:7]([CH:12]([C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:13][CH2:14][CH2:15][CH3:16])C(OC)=O>CS(C)=O>[CH3:4][O:5][C:6](=[O:25])[CH2:7][CH:12]([C:17](=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 962Water2×HCID 5234Sodium ChlorideHCID 66757258HCID 66757258, compound

Product 1

HCID 66756925HCID 66756925, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

Water (3 ml, 166 mmol) and NaCl (5.3 g, 90.2 mmol) are added to a solution of 2-(1-benzoyl-pentyl)-malonic acid dimethyl ester (25.0 g, 81.7 mmol) in DMSO (150 mL). The mixture is heated at 150° C. for 6 hours. Water (450 mL) is added and the mixture is extracted with EtOAc (4×150 mL). The combined extracts are washed with brine (300 mL), dried (Na2,SO4), and evaporated, to provides 3-Benzoyl-heptanoic acid methyl ester as a light yellow oil. LC-MS (M+1) 249. This compound without further purification is used directly to the next step.

Workup

  1. extractionthe mixture is extracted with EtOAc (4×150 mL)
  2. washThe combined extracts are washed with brine (300 mL)
  3. dry with materialdried (Na2,SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-906d1fdbf4b645b6b6472104709f1279
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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