Diethyl Ether → HCID 18948954, compound

HRID 1768619Notes

Reaction equation

HRID 1768619 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[C:17]3C(OC)=O)(=[O:11])=[O:10])[O:4][N:3]=1.[CH3:26][Mg]Br.CC[O:31][CH2:32][CH3:33]>O1CCCC1>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[C:13]3[C:18](=[C:17]([C:32]([OH:31])([CH3:33])[CH3:26])[CH:16]=[CH:15][CH:14]=3)[CH:19]=[CH:20][CH:21]=2)(=[O:11])=[O:10])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10067069HCID 10067069, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 18948954HCID 18948954, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 32 (0.99 g, 2.75 mmol) in dry tetrahydrofuran (50 mL) was added methyl magnesium bromide (4.58 mL of a 3M solution in ether, 13.7 mmol). The solution was heated at reflux for 75 minutes, quenched with 5% aqueous potassium hydrogen sulfate and extracted with ethyl acetate and the organic phase was washed with brine, dried (magnesium sulfate) and evaporated. The residue was combined with the product of a previous reaction (0.55 mmol scale) to afford 1.26 g of off-white foamy solid. Chromatography on silica (flash; 75% ethyl acetate/hexanes) afforded 0.28 g (24%) of Example 35 as a white foamy solid (melting point 97°-101° C.) as well as 0.40 g of slightly less pure material.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 75 minutes
  3. customquenched with 5% aqueous potassium hydrogen sulfate
  4. extractionextracted with ethyl acetate
  5. washthe organic phase was washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated
  8. customThe residue was combined with the product of a previous reaction (0.55 mmol scale)

Sources & evidence

ORD record
ord-6a61c4a1aa1f4cb49807f8fce5eba361
Source dataset
uspto-grants-1995_01
Patent number
US05378715

Reaction notes

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