Ethyl Acetate → HCID 21570391, compound

HRID 2371791Notes

Reaction equation

HRID 2371791 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14].O([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([NH:33][C:34](=[O:41])[CH2:35][CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:31]=2)[CH:26]=[CH:25][CH:24]=1)S(C(F)(F)F)(=O)=O.C(OCC)(=O)C>O1CCCC1.[Zn].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:36]1([CH2:35][C:34]([NH:33][C:30]2[CH:31]=[C:32]3[C:27]([CH:26]=[CH:25][CH:24]=[C:23]3[CH2:2][C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=3[O:13][CH3:14])=[CH:28][CH:29]=2)=[O:41])[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 19906388HCID 19906388, compound

Product 1

HCID 21570391HCID 21570391, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of activated zinc dust (806 mg), methyl 4-bromomethyl-3-methoxybenzoate (2.14 g) and tetrahydrofuran (15 ml) was stirred for 18 h. To the reaction was added dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (76 mg). After stirring for 15 min, 7-(cyclopentylacetamido)naphth-1-yl triflate (830 mg) in tetrahydrofuran (10 ml) was added and the mixture was stirred for 72 h. The mixture was added to 100 ml of ethyl acetate and the ethyl acetate solution was washed (1N HCl, brine), dried (MgSO4) and evaporated. The residue was flash chromatographed, eluting with ether:petroleum ether (2:8,4:6, and 1:4, successively), to give a white solid. Recrystallization from methylene chloride and petroleum ether gave the title compound as a colorless solid (705 mg, 79%); mp 172.5°-174.5° C.

Workup

  1. stirringAfter stirring for 15 min
  2. stirringthe mixture was stirred for 72 h
  3. washthe ethyl acetate solution was washed (1N HCl, brine)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customchromatographed
  7. washeluting with ether:petroleum ether (2:8,4:6, and 1:4
  8. customsuccessively), to give a white solid
  9. customRecrystallization from methylene chloride and petroleum ether

Sources & evidence

ORD record
ord-7b9eb81c5d2042749ceaeb089c1c37dd
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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