Diethyl Ether → HCID 19887628, compound

HRID 654475Notes

Reaction equation

HRID 654475 reaction equation
C([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][C:18]([O:20]C)=O)[CH:9]=1)C1C=CC=CC=1.[CH2:22]([Mg]Cl)[CH:23]([CH3:25])[CH3:24].CCOCC>C1COCC1>[CH3:22][CH:23]([CH3:25])[CH2:24][C:18](=[O:20])[CH2:17][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 54285481HCID 54285481, compoundHCID 178418368HCID 178418368, compound

Product 1

HCID 19887628HCID 19887628, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl indol-1-ylacetate (1.13 g, 5.9 mmol) from Example 1, Step 1, in THF at -78° C. was added dropwise a solution of 2M isobutyl magnesium chloride in Et2O (3.3 mL, 6.6 mmol). The reaction mixture was warmed up to 0° C. and kept at this temperature until the starting material disappeared. The reaction mixture was quenched with a 0.5M solution of Na and K tartrate and extracted with EtOAc. The extract was washed with a solution of NH4OAc, dried over MgSO4 and evaporated to dryness. The crude residue was chromatographed on flash silica gel column eluting with EtOAc-hexane (1:9) to afford the pure title product.

Workup

  1. customThe reaction mixture was quenched with a 0.5M solution of Na and K tartrate
  2. extractionextracted with EtOAc
  3. washThe extract was washed with a solution of NH4OAc
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe crude residue was chromatographed on flash silica gel column
  7. washeluting with EtOAc-hexane (1:9)

Sources & evidence

ORD record
ord-04740d4a3c0b47449f5291c5693b2d6e
Source dataset
uspto-grants-1992_07
Patent number
US05132319

Reaction notes

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