Diethyl Ether → HCID 14772476, compound

HRID 1084470Notes

Reaction equation

HRID 1084470 reaction equation
[Mg].[CH3:2]I.C[Mg]I.[NH:7]([C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH2:13][O:14]C2=O)[C:8]([CH3:10])=[O:9].[Cl-].[NH4+].C([O:25][CH2:26][CH3:27])C>O1CCCC1>[CH3:2][C:26]([OH:25])([CH3:27])[C:17]1[CH:18]=[CH:19][CH:20]=[C:11]([NH:7][C:8]([CH3:10])=[O:9])[C:12]=1[CH2:13][OH:14]

Participants

8

Reactant 6

HCID 3283Diethyl Ether3×HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 12284648HCID 12284648, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 14772476HCID 14772476, compound

Reagents, catalysts & solvents 1

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 56 g of methyl iodide in 120 ml of diethyl ether. The mixed solution was heated for 15 minutes under refluxing and cooled. The solution of methylmagnesium iodide 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 dried and concentrated to obtain an oily substance. The oily substance was purified by silica gel column chromatography to obtain 7.2 g of α,α-dimethyl-2-hydroxymethyl-3-acetaminobenzyl alcohol in the white crystal form. m.p. 137.9 ° C.

Workup

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

Sources & evidence

ORD record
ord-942d3c0c56ba4951ad418e425f7aeed7
Source dataset
uspto-grants-1991_04
Patent number
US05004816

Reaction notes

Loading…