Diethyl phenylmalonate → HCID 45790788, compound

HRID 1780210Notes

Reaction equation

HRID 1780210 reaction equation
[K].[O-]CCCC.[C:7]1([CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:25][CH2:26][O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1>CN(C=O)C>[C:7]1([C:13]([CH2:25][CH2:26][O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 66514Diethyl phenylmalonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 5462222PotassiumHCID 12476378Butan-1-olate

Product 1

HCID 45790788HCID 45790788, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
70 °C

Procedure

Potassium t.butoxide (112 g, 1M) in DMF (800 ml) was treated with diethyl phenylmalonate (236 g, 1M) in DMF (200 ml) then with 1-bromo-2-tetrahydropyranyloxy-ethane (209 g, 1M) in DMF (200 ml). The reaction was heated to 70° C. After 5 hours the reaction was cooled to room temperature, quenched on to water (2.5 l) and 2N HCl (500 ml), and extracted with IPE (1 l, then 500 ml). The organic extracts were washed with water, dried and evaporated to give the title compound (351 g, 96%). Glc 93%+7% unchanged diethylphenylmalonate.

Workup

  1. temperatureAfter 5 hours the reaction was cooled to room temperature
  2. customquenched on to water (2.5 l) and 2N HCl (500 ml)
  3. extractionextracted with IPE (1 l
  4. washThe organic extracts were washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ffbbcb507ada4a0ba61a735eac8d0149
Source dataset
uspto-grants-1997_05
Patent number
US05629432

Reaction notes

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