Ethyl Bromide → HCID 15036289, compound

HRID 728579Notes

Reaction equation

HRID 728579 reaction equation
[Mg].[CH2:2](Br)[CH3:3].[CH2:5]([Mg]Br)[CH3:6].[NH:9]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][O:16][C:17]2=[O:18])[C:10]([CH3:12])=[O:11].[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH2:5]([C:17]([OH:18])([CH2:2][CH3:3])[C:19]1[CH:20]=[CH:21][CH:22]=[C:13]([NH:9][C:10]([CH3:12])=[O:11])[C:14]=1[CH2:15][OH:16])[CH3:6]

Participants

8

Reactant 5

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 12284648HCID 12284648, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 15036289HCID 15036289, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 9.5 g of metallic magnesium and 60 ml of diethyl ether was slowly added with stirring a solution of 43 g of ethyl bromide in 120 ml of diethyl ether. The mixed solution was heated for 15 minutes under refluxing and left to stand for cooling. The solution of ethylmagnesium bromide thus prepared above in ether was slowly added with stirring at inner temperature of below 10° C. to a solution of 7.5 g of 4-acetaminophthalide in 120 ml of tetrahydrofuran, followed by stirring at room temperature overnight. After the reaction was over, the reaction mixture was poured into aqueous ammonium chloride solution (saturated) under ice cooling and extracted twice with 400 ml of ethyl acetate. The combined extracts were concentrated to obtain an oily substance. The oily substance was purified by silica gel column chromatography to obtain 8.0 g of α,α-diethyl-2-hydroxymethyl-3-acetaminobenzyl alcohol in the colorness oily substance.

Workup

  1. additionwas slowly added
  2. temperatureThe mixed solution was heated for 15 minutes
  3. temperatureunder refluxing
  4. waitleft
  5. temperaturefor cooling
  6. additionwas slowly added
  7. extractionextracted twice with 400 ml of ethyl acetate
  8. concentrationThe combined extracts were concentrated
  9. customto obtain an oily substance
  10. customThe oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7dbd196296d445e8b0df5226befd1158
Source dataset
uspto-grants-1991_09
Patent number
US05049575

Reaction notes

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