Ethyl formate → HCID 18319635, compound

HRID 1699373Notes

Reaction equation

HRID 1699373 reaction equation
[O-]CC.[Na+].I[C:6]1[C:16]2[O:15][CH2:14][CH2:13][C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:25]([O:24][C:22]([C:6]1[C:16]2[O:15][CH2:14][CH2:13][C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:23])[CH3:26]

Participants

6

Reactant 3

HCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 18319552HCID 18319552, compound

Product 1

HCID 18319635HCID 18319635, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of sodium ethoxide (1.7 ml, 20% in ethanol) and dichlorobis(triphenylphosphine)palladium(II) (14 mg) in dichloromethane (7 ml) was added a mixture of ethyl 2,3-dihydro-9-iodo-1-benzoxepin-4-carboxylate (0.69 g) and ethyl formate (0.28 ml) at ambient temperature under nitrogen atmosphere. The reaction mixture was stirred at 40° C. for 3 hours and filtered off. The filtrate was partitioned between diethyl ether and 1N hydrochloric acid. The organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by medium pressure liquid chromatography (silica gel) using a mixture of ethyl acetate and n-hexane (1:19) as an eluent to give a solid of ethyl 2,3-dihydro-9-ethoxycarbonyl-1-benzoxepin-4-carboxylate (120 mg).

Workup

  1. additionwas added
  2. filtrationfiltered off
  3. customThe filtrate was partitioned between diethyl ether and 1N hydrochloric acid
  4. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by medium pressure liquid chromatography (silica gel)
  8. additiona mixture of ethyl acetate and n-hexane (1:19) as an eluent

Sources & evidence

ORD record
ord-c0705d79d988482492ae2f6ed8dc4030
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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