Hexane → HCID 58914663, compound

t-butylacetoacetate (1.5 mL, 9.2 mmol) was added dropwise over 2 minutes to a stirred suspension of sodium hydride (60%; 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 (2 H), 6.93 (2 H), 3.33 (2 H), 2.85 (4 H), 1.45 (9 H).

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)

ORD record

ord-f77004e8f4c04fc7b04499b3ced59a20

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07250439B2