Tetrahydrofuran → HCID 57835422, compound

HRID 730981Notes

Reaction equation

HRID 730981 reaction equation
C(O[C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:8]=2[CH:7]=1)=[O:5])C.[CH2:17]([Mg]Br)[CH3:18].[CH2:21]1COC[CH2:22]1>>[CH3:16][O:15][C:13]1[CH:12]=[CH:11][C:9]2[S:10][C:6]([C:4]([OH:5])([CH2:17][CH3:18])[CH2:21][CH3:22])=[CH:7][C:8]=2[CH:14]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 13527237HCID 13527237, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 57835422HCID 57835422, compoundYield 97%

Procedure

5-Methoxy-benzo[b]thiophene-2-carboxylic acid ethyl ester (4.13 g, 17.5 mmol) in THF (100 mL) at −78° C. is treated with ethylmagnesium bromide (17.5 mL, 3.0 M). The reaction mixture is allowed to warm to RT over 30 min and is stirred for 10 min. The mixture is quenched with water (40 mL) and acidified with HCl (50 mL, 1.0 M). THF is removed under vacuum, and the residue is extracted with EtOAc (2×40 mL). The organic layer is dried over Na2SO4, concentrated, and purified using silica gel column chromatography (10% EtOAc/Hex) to give the title compound (4.53 g, 97%).

Workup

  1. customThe mixture is quenched with water (40 mL)
  2. customTHF is removed under vacuum
  3. extractionthe residue is extracted with EtOAc (2×40 mL)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-1c63a64dcf4f44abae08def7c307537b
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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