Formaldehyde → HCID 57864760, compound

HRID 2425531Notes

Reaction equation

HRID 2425531 reaction equation
[C:1]1([C@@H:7]([NH:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]=O.CO.[C:22]([O-:25])([O-])=O.[K+].[K+]>O>[CH3:18][O:25][CH2:22][N:12]([CH2:13][Si:14]([CH3:16])([CH3:15])[CH3:17])[C@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 11430Potassium CarbonateHCID 67244960HCID 67244960, compound

Product 1

HCID 57864760HCID 57864760, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

(R)-methyl 2-phenyl-2-((trimethylsilyl)methylamino)acetate (1.0 g, 3.98 mmol) was added to a mixture of 37% aqueous formaldehyde (784 mg) and methanol (310 mg) while stirring at 0° C. After two hours K2CO3 (1.0 g) was added and the mixture was stirred for an additional hour. Then, water (10 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The combined organic layers were dried with Na2SO4. Concentration under vacuum gave the crude (R)-methyl 2-((methoxymethyl)((trimethylsilyl)methyl)amino)-2-phenylacetate as an oil (theor. max. 3.98 mmol). The product was directly used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred for an additional hour
  2. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-dda77427f4d14fcf916ec3bf067696ad
Source dataset
uspto-grants-2011_06
Patent number
US07964739B2

Reaction notes

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