Methanol → HCID 22168547, compound

HRID 1709943Notes

Reaction equation

HRID 1709943 reaction equation
CO.O=[C:4]([CH3:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1.[C:18]([BH3-])#[N:19].[Na+].C(N(CC)CC)C>Cl>[CH3:18][NH:19][CH:4]([CH3:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydride2×HCID 13553580Methyl [4-(2-oxopropyl)phenyl]acetate

Product 1

HCID 22168547HCID 22168547, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 25 mL of methanol 0.59 g of methyl 4-(2-oxopropyl)phenylacetate, prepared above, was added and dissolved. Then with stirring the following were added: 2.0 g-methylamine hydrochloride, 0.3 g sodium cyanoborohydride, and 0.3 mL of triethylamine. After approximately 12 hours an additional 0.1 g of sodium cyanoborohydride was added to the mixture. After 3 hours more, the reaction was diluted with 100 mL of 0.1 M hydrochloric acid, washed with diethylether, and the resulting aqueous phase was basified to a pH of 12 by addition of 5 mL portions of 1 N sodium hydroxide solution. This was extracted three times with 100 mL portions of diethylether, combined extracts washed with brine and dried. The solvents were removed in vacuo to yield 0.44 g of a light yellow oil.

Workup

  1. additionwas added
  2. dissolutiondissolved
  3. additionfollowing were added
  4. washwashed with diethylether
  5. additionthe resulting aqueous phase was basified to a pH of 12 by addition of 5 mL portions of 1 N sodium hydroxide solution
  6. extractionThis was extracted three times with 100 mL portions of diethylether
  7. washcombined extracts washed with brine
  8. customdried
  9. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-76e1055c052a40aab824905b7c7e4b3d
Source dataset
uspto-grants-1990_08
Patent number
US04952336

Reaction notes

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