Dimethyl malonate → HCID 10049384, compound

HRID 257638Notes

Reaction equation

HRID 257638 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[O:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1.[C:26]([O:33][CH3:34])(=[O:32])[CH2:27][C:28]([O:30][CH3:31])=[O:29].CC(C)([O-])C.[K+].O1CCCC1>Cl.C(OCC)C>[C:14]1([C:12]2[N:13]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH:27]([C:26]([O:33][CH3:34])=[O:32])[C:28]([O:30][CH3:31])=[O:29])[O:10][C:11]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 7943Dimethyl malonateHCID 8028TetrahydrofuranHCID 9978168HCID 9978168, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10049384HCID 10049384, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 2-(7-bromoheptyl)-4,5-diphenyloxazole (10.00 g, 25 mmol), dimethyl malonate (9.95 g, 8.60 mL, 75 mmol), potassium tert-butoxide (8.44 g, 75 mmol), Eighteen Crown 6 ether (catalytic amount) and tetrahydrofuran (200 mL) was heated to reflux under an atmosphere of nitrogen. After 17.5 hours, the mixture was cooled, diluted with 2N hydrochloric acid solution and extracted with CH2Cl2. The combined extracts were dried over sodium sulfate and concentrated in vacuo to leave an oil. Chromatography on a column of silica gel using a mixture of hexanes and diethyl ether (9:1) as eluent afforded dimethyl 2-[7-(4,5-diphenyl-2-oxazolyl)heptyl]propanedioate (9.47 g, 83%) as an oil. An analytical sample (hydrated) was prepared by rechromatographing a 3.28 g sample on silica gel using a mixture of hexane and diethyl ether (4:1) as the mobile phase.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under an atmosphere of nitrogen
  3. temperaturethe mixture was cooled
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto leave an oil

Sources & evidence

ORD record
ord-7b44305d287e4bacb9a856adf8d8f458
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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