Dimethyl malonate → HCID 14834356, compound

HRID 1086961Notes

Reaction equation

HRID 1086961 reaction equation
C(OC)(=O)[CH2:2][C:3](OC)=[O:4].CC[O-].[Na+].[O:14]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:23]=[C:22]([CH:24]=[CH:25][C:26](=[O:28])[CH3:27])[O:21][N:20]=2)[CH2:15]1>CO>[OH:4][C:3]1[CH2:2][CH:24]([C:22]2[O:21][N:20]=[C:19]([CH:16]3[CH2:17][CH2:18][O:14][CH2:15]3)[CH:23]=2)[CH2:25][C:26](=[O:28])[CH:27]=1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 2723922Sodium ethoxideHCID 67885215HCID 67885215, compound

Product 1

HCID 14834356HCID 14834356, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

10.6 g of dimethyl malonate in 300 ml of methanol were initially taken, and 14.4 g of a 30% strength sodium ethylate solution in methanol were added at room temperature. Thereafter, 16.0 g of 4-[tetrahydrofur-3-yl-isoxazol-5-yl]-3-buten-2-one were added and the mixture was stirred for 1 day at 25° C. The residue which remained after the solvent had been removed was taken up in 10% strength sodium hydroxide solution and stirred for 24 hours at 25° C. The sodium hydroxide phase was washed with methyl tert-butyl ether, acidified to pH 2 with concentrated hydrochloric acid and then heated at 85° C. for 2 hours. The solid formed was filtered off, washed with water and dried. 12.3 g of a beige solid of melting point 142°-144° C. were obtained.

Workup

  1. customhad been removed
  2. stirringstirred for 24 hours at 25° C
  3. washThe sodium hydroxide phase was washed with methyl tert-butyl ether
  4. temperatureheated at 85° C. for 2 hours
  5. customThe solid formed
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-e53a7891ca0b430da6937351b7c63260
Source dataset
uspto-grants-1991_07
Patent number
US05034047

Reaction notes

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