Tetrahydrofuran → HCID 57810548, compound

HRID 2106425Notes

Reaction equation

HRID 2106425 reaction equation
C(O[C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:9]=2[CH:10]=1)=[O:5])C.[CH2:16]([Mg]Br)[CH3:17].[CH2:20]1COC[CH2:21]1>>[Br:15][C:12]1[CH:13]=[CH:14][C:8]2[O:7][C:6]([C:4]([OH:5])([CH2:16][CH3:17])[CH2:20][CH3:21])=[CH:10][C:9]=2[CH:11]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 735184Ethyl (5-bromobenzofuran)-2-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 57810548HCID 57810548, compoundYield 88%

Procedure

To a stirred solution of 5-bromo-benzofuran-2-carboxylic acid ethyl ester (24.3 g, 90.3 mmol) in THF (300 mL) at −40° C. is added ethyl magnesium bromide (90.3 mL, 3.0 M). The reaction is allowed to warm to RT and stirred for 2 h before quenched with water and HCl (1.0 M) till pH˜2. The THF is removed in vacuum and the mixture is extracted with EtOAc (200 mL, 100 mL). The organic layer is dried over Na2SO4, concentrated, purified on column chromatography (10-15% EtOAc/Hex), to give the title compound as an oil (22.4 g, 88%)

Workup

  1. custombefore quenched with water and HCl (1.0 M) till pH˜2
  2. customThe THF is removed in vacuum
  3. extractionthe mixture is extracted with EtOAc (200 mL, 100 mL)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified on column chromatography (10-15% EtOAc/Hex)

Sources & evidence

ORD record
ord-b08511f6cc20455e8298cd09f4d6cd53
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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