Diethyl Malonate → HCID 67099636, compound

HRID 1868885Notes

Reaction equation

HRID 1868885 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Mg+2].[Cl-].[Cl-].[C:15]1([C:21]2([C:27](O)=[O:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.S(Cl)(Cl)=O>C(#N)C.CCOC(C)=O>[C:15]1([C:21]2([C:27]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[O:28])[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 24386Thionyl ChlorideHCID 41385534-phenyltetrahydro-2H-pyran-4-carboxylic acidHCID 5360315Magnesium Chloride

Product 1

HCID 67099636HCID 67099636, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl malonate (3.96 mL, 26.2 mmol) in ACN (52.4 mL) at 0° C. was added MgCl2 (2.74 g, 28.8 mmol) in one portion. TEA (7.30 mL, 52.4 mmol) was added dropwise, and the reaction mixture was allowed to warm to ambient temperature and stirred for 3 hours. 4-Phenyl-tetrahydro-2H-pyran-4-carboxylic acid (5.13 g, 24.9 mmol) was converted to the acid chloride by addition of thionyl chloride and reaction at 65° C. for 1 hour. The resulting acid chloride solution was then concentrated in vacuo, dissolved in ACN, and added to the initial reaction mixture. The resulting mixture was stirred at ambient temperature for 2 hours and then diluted with 200 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 2 times with 75 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the title compound without further purification. MS m/e=349 (M+H)+.

Workup

  1. concentrationThe resulting acid chloride solution was then concentrated in vacuo
  2. dissolutiondissolved in ACN
  3. additionadded to the initial
  4. customreaction mixture
  5. stirringThe resulting mixture was stirred at ambient temperature for 2 hours
  6. additionadded to a separatory funnel
  7. custompartitioned with water
  8. washwashed 2 times with 75 mL of water
  9. customseparated
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99696d952f8646a79c8faba2e404960a
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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