Diethyl Malonate → HCID 67822321, compound

HRID 1463762Notes

Reaction equation

HRID 1463762 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10]C)=[O:8])C.C[O-].[Na+].Cl[CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1>>[CH3:2][O:4][C:5](=[O:12])[CH:6]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 4

HCID 7761Diethyl MalonateHCID 1704882H-Pyran, 2-(4-chlorobutoxy)tetrahydro-HCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 67822321HCID 67822321, compound

Procedure

7.9 g (0.3 mol) of sodium in a stream of nitrogen was placed in a 500-ml 3-necked flash with reflux condenser, drying tube and dropping funnel with pressure equalisation. Next, 250 ml of anhydrous methanol was carefully added dropwise and agitated until the sodium had completely dissolved. A methanolic solution of 95.4 g (0.58 mol) malonic acid diethyl ester was added very slowly dropwise to the still-warm sodium methanolate solution. At the end of the addition process, the mixture was reflux-boiled for a further hour, after which 0.5 mol of 1-chloro-4-tetrahydro-pyranyloxybutane was slowly added dropwise. The mixture was then reflux-boiled overnight.

Workup

  1. temperaturewith reflux condenser
  2. customdrying tube
  3. additionNext, 250 ml of anhydrous methanol was carefully added dropwise
  4. dissolutionhad completely dissolved
  5. waitAt the end of the addition process, the mixture was reflux-boiled for a further hour
  6. customreflux-boiled overnight

Sources & evidence

ORD record
ord-427ed6e2fa48496a89a60155c622698e
Source dataset
uspto-grants-1994_04
Patent number
US05302370

Reaction notes

Loading…