Ethyl 2-(diphenylmethyleneamino)acetate → HCID 15610108, compound

HRID 1167387Notes

Reaction equation

HRID 1167387 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:32][C:33]([CH3:35])=[CH2:34]>C1COCC1.C(OCC)(=O)C>[C:8]1([C:7](=[N:6][CH:5]([CH2:34][C:33]([CH3:35])=[CH2:32])[C:4]([O:3][CH2:1][CH3:2])=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 3577853-Bromo-2-methyl-1-propeneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 15610108HCID 15610108, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-(diphenylmethylene)glycine ethyl ester (available from Aldrich Chemical Co., Milwaukee, Wis.) (50.0 g, 187 mmol) in dry THF (200 mL) at −78° C. under argon was added a 1.0 M solution of lithium bis(trimethylsilyl)amide (Li HMDS; 210 mL, 0.2 mol) in THF over a period of 45 min (“1.A, Scheme A). After 0.5 hour at −78° C., 3-bromo-2-methylpropene (18.91 mL, 187 mmol) was added dropwise to the orange-yellow suspension. After the addition was complete, the reaction mixture was stirred for an additional 0.5 hour at 0° C. and then allowed to warm to room temperature. After 1 hour the reaction mixture was concentrated under reduced pressure to give an orange-colored oil. The crude material was dissolved in ethyl acetate (EA) (600 mL), washed with brine (100 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure to give the desired compound (60 g, 99%), which was used for the next step without further purification.

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. concentrationAfter 1 hour the reaction mixture was concentrated under reduced pressure
  4. customto give an orange-colored oil
  5. washwashed with brine (100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1ae02f00ffc4d03bb59f65066cfaad9
Source dataset
uspto-grants-2003_09
Patent number
US06617426B1

Reaction notes

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