Hexane → HCID 58914663, compound

HRID 2382917Notes

Reaction equation

HRID 2382917 reaction equation
[C:1]([O:5][C:6](=[O:11])[CH2:7][C:8]([CH3:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C([Li])CCC.CCCCCC.[I:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1>O1CCCC1>[C:1]([O:5][C:6](=[O:11])[CH2:7][C:8](=[O:9])[CH2:10][CH2:30][C:29]1[CH:32]=[CH:33][C:26]([I:25])=[CH:27][CH:28]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 8058HexaneHCID 15538Tert-butyl acetoacetateHCID 24758Sodium hydrideHCID 9542584-Iodobenzyl bromideHCID 178418339Butyllithium

Product 1

HCID 58914663HCID 58914663, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

t-butylacetoacetate (1.5 mL, 9.2 mmol) was added dropwise over 2 minutes to a stirred suspension of sodium hydride (60% mineral oil suspension; 400 mg, 10.0 mmol) in tetrahydrofuran at 0° C. under nitrogen. After stirring for 10 minutes n-butyl lithium in hexane (1.6 M; 6.0 mL, 9.6 mmol) was added then stirring continued for a further ten minutes. The resulting solution was treated dropwise with a solution of 4-iodobenzyl bromide (2.97 g, 10.0 mmol) in tetrahydrofuran (4 mL) and then warmed to room temperature. The reaction was stirred for 40 minutes at room temperature and then quenched with 6 M HCl (5 mL). The resulting mixture was extracted with diethyl ether (3×50 mL). The organic phases were combined, washed with brine (50 mL) and dried (MgSO4) then the solvent evaporated under reduced pressure. The residue was purified via flash chromatography on silica gel (1:20 to 1:10 ethyl acetate/cyclohexane) to give the title compound (1.88 g, 54%) as a yellow oil. LC/MS: 3.66 min; z/e 375, calcd (M+1) 375. 1H NMR (400 MHz; CDCl3): 7.6 (2H), 6.93 (2H), 3.33 (2H), 2.85 (4H), 1.45 (9H).

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 6 M HCl (5 mL)
  5. extractionThe resulting mixture was extracted with diethyl ether (3×50 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated under reduced pressure
  9. customThe residue was purified via flash chromatography on silica gel (1:20 to 1:10 ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-2714f13b4c964429a35a77a7b1420bd1
Source dataset
uspto-grants-2012_09
Patent number
US08263602B2

Reaction notes

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