Diethyl Malonate → HCID 86750891, compound

HRID 1781542Notes

Reaction equation

HRID 1781542 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH3:14][S:15]([O:18][C:19]1[C:27]([CH2:28]/[CH:29]=[C:30](/[Cl:33])\[CH2:31]Br)=[C:26]([O:34][CH3:35])[C:25]([CH3:36])=[C:24]2[C:20]=1[C:21](=[O:37])[O:22][CH2:23]2)(=[O:17])=[O:16]>C1COCC1>[CH3:14][S:15]([O:18][C:19]1[C:27]([CH2:28]/[CH:29]=[C:30](/[Cl:33])\[CH2:31][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[C:26]([O:34][CH3:35])[C:25]([CH3:36])=[C:24]2[C:20]=1[C:21](=[O:37])[O:22][CH2:23]2)(=[O:16])=[O:17]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 86750892HCID 86750892, compound

Product 1

HCID 86750891HCID 86750891, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl malonate (113 mg) was added to a suspension of 50% NaH (35 mg) in THF (3 ml) at 0° C. and the mixture stirred for 30 minutes. To this solution was added (E)-4-(1,3-dihydro-4-methanesulfonyloxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-1-bromo-2-chlorobut-2-ene (280 mg) in THF (10 ml). The ice bath was removed and the mixture was stirred at room temperature for 2 hours. The mixture was added to water (30 ml), the aqueous and organic phases separated, and the aqueous phase was extracted once with ethyl acetate (20 ml). The combined organic layers were dried over Na2SO4, evaporated and the residue passed through a short column (silica gel, hexanes-EtOAc 8:2) affording 190 mg of ethyl (E)-6-(4-methanesulfonyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) -4-chloro-2-ethoxycarbonyl-4-hexenoate as a colorless oil.

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. additionThe mixture was added to water (30 ml)
  4. customthe aqueous and organic phases separated
  5. extractionthe aqueous phase was extracted once with ethyl acetate (20 ml)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-345a467f4df54eeeb4868c55d548a875
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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