Diisopropylamine → 5-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

HRID 2396024Notes

Reaction equation

HRID 2396024 reaction equation
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH3:13][O:14][C:15](=[O:25])[CH2:16][N:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.BrCCC=C.CN(C)P(N(C)C)(N(C)C)=O>O1CCCC1.CCCCCC.O>[CH3:13][O:14][C:15](=[O:25])[CH:16]([CH2:11][CH2:10][CH:9]=[CH2:8])[N:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 12679HexamethylphosphoramideHCID 21241Homoallyl bromideHCID 4169153Methyl [(phenylmethylidene)amino]acetateHCID 178418339Butyllithium

Product 1

HCID 120394615-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve diisopropylamine (15.4 mL, 110 mmol) in tetrahydrofuran (250 mL), place under a nitrogen atmosphere and cool to -78° C. Add n-butyllithium (39 mL of a 2.7M solution in hexane, 105 mmol). Stir for 30minutes and add, by dropwise addition, a solution of N-(phenylmethylene)glycine methyl ester (17.7 g, 100 mmol) in tetrahydrofuran (25 mL). Stir for 15 minutes and add 4-bromobutene (13.5 g, 100 mmol) and allow to warm slowly to room temperature. Add hexamethylphosphoramide (20 mL, 100 mmol) and stir under a nitrogen atmosphere for 3 hours. Pour into water, extract into ethyl ether and washwith brine several times. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as an amber oil (25 g).

Workup

  1. additionadd, by dropwise addition
  2. stirringStir for 15 minutes
  3. temperatureto warm slowly to room temperature
  4. extractionextract into ethyl ether
  5. dry with materialDry (MgSO4)
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-8b66c292f8094b73ab0f411620dbdb24
Source dataset
uspto-grants-1996_02
Patent number
US05491143

Reaction notes

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