Tert-butyl acetoacetate → HCID 66671407, compound

HRID 2371101Notes

Reaction equation

HRID 2371101 reaction equation
[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>O1CCCC1.CCCCCC>[C:8]([O:7][C:1](=[O:6])[CH2:2][C:3](=[O:4])[CH2:5][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([Br:19])=[CH:21][CH:22]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 15538Tert-butyl acetoacetateHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 178418339Butyllithium

Product 1

HCID 66671407HCID 66671407, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

tert-Butyl acetoacetate (23.8 ml) was added dropwise over 15 minutes to a stirred suspension of sodium hydride (8.9 mg) in tetrahydrofuran at 0° C. under nitrogen atmosphere. After stirring for 20 minutes n-butyl lithium in hexane (111 ml) was added then stirring continued for a further ten minutes. The resulting solution was treated dropwise with a solution of 4-bromobenzyl bromide (14.19 g) in tetrahydrofuran (100 ml) and then warmed to room temperature. The reaction was stirred for 40 minutes at room temperature and then quenched with HCl (6M, 5 ml). The resulting mixture was extracted with diethyl ether. The organic phases were combined, washed with brine and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure. The residue was thus obtained was purified via flash chromatography using 5% ethyl acetate in hexane as eluant to furnish the title compound (37 g).

Workup

  1. additionwas added
  2. waitcontinued for a further ten minutes
  3. stirringThe reaction was stirred for 40 minutes at room temperature
  4. customquenched with HCl (6M, 5 ml)
  5. extractionThe resulting mixture was extracted with diethyl ether
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was thus obtained
  10. customwas purified via flash chromatography

Sources & evidence

ORD record
ord-4cb117dd6fd04a629b479969e2c05297
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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