Iodoethane → HCID 10805871, compound

HRID 1993736Notes

Reaction equation

HRID 1993736 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([O:13][C:14](=[O:30])[CH2:15][N:16]=[C:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:12].C(=O)=O.C[C:35]([CH3:37])=O.I[CH2:39][CH3:40]>O1CCCC1>[C:18]1([C:17](=[N:16][C:15]([CH2:35][CH3:37])([CH2:39][CH3:40])[C:14]([O:13][CH2:11][CH3:12])=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6340Iodoethane2×HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 3251421Potassium bis(trimethylsilyl)amide2×HCID 18522661Acetone cardice4×

Product 1

HCID 10805871HCID 10805871, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of potassium bis(trimethylsilyl)amide (15.02 g, 75.3 mmol) in 80 mL of anhydrous tetrahydrofuran was added under nitrogen dropwise over 30 min to a solution of N-(diphenylmethylene)glycine ethyl ester (18.34 g, 68.6 mmol) in 300 mL of anhydrous tetrahydrofuran at dry ice-acetone temperature. After the addition, the reaction was stirred at dry ice-acetone temperature for 1 h. Iodoethane (6.60 mL, 82.5 mmol) was added over 2 min. The cooling bath was removed and the stirring continued for 3.5 h. Reaction cooled to dry ice-acetone temperature. A solution of potassium bis(trimethylsilyl)amide (15.02 g, 75.3 mmol) in 100 mL of anhydrous tetrahydrofuran was added dropwise over 30 min. After the addition, the reaction was stirred at dry ice-acetone temperature for 1 h. Iodoethane (6.60 mL, 82.5 mmol) was added over 2 min. The cooling bath was removed and the reaction stirred for 17 h. The reaction was concentrated under reduced pressure to remove most of the tetrahydrofuran. The residue was partitioned between methylene chloride and water. The organic layer was separated and the aqueous layer extracted three times with methylene chloride. The combined extracts were washed with saturated sodium chloride, dried (anhydrous MgSO4), filtered and the solvent removed under reduced pressure to give ethyl 2-[(diphenylmethylene)amino]-2-ethylbutanoate (21.50 g, 97%) as a yellow oil, MS (ESI) m/z 324 [M+H]+.

Workup

  1. additionAfter the addition
  2. customThe cooling bath was removed
  3. customReaction
  4. additionAfter the addition
  5. customThe cooling bath was removed
  6. concentrationThe reaction was concentrated under reduced pressure
  7. customto remove most of the tetrahydrofuran
  8. customThe residue was partitioned between methylene chloride and water
  9. customThe organic layer was separated
  10. extractionthe aqueous layer extracted three times with methylene chloride
  11. washThe combined extracts were washed with saturated sodium chloride
  12. dry with materialdried (anhydrous MgSO4)
  13. filtrationfiltered
  14. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ebe72d38a2844c0da68a284c0fae2c62
Source dataset
uspto-grants-2010_01
Patent number
US07652018B2

Reaction notes

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