Sodium hydride → 1-Tert-butyl 5-ethyl 2-[(acetyloxy)acetyl]pentanedioate

HRID 2250635Notes

Reaction equation

[H-].[Na+].[C:3]([O:6][CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:5])[CH3:4].I[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1>[C:3]([O:6][CH2:7][C:8]([CH:9]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:17])(=[O:5])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 60% NaH (1.02 g) in THF (50 mL) was added tert-butyl 4-(acetyloxy)-3-oxobutanoate (5.00 g) under ice-water cooling and the mixture was stirred at 0° C. for 0.5 hour. To this added ethyl 3-iodopropanoate (5.54 g) and the mixture was stirred at 50° C. for 8 hours. The mixture was partitioned between AcOEt and water. The organic layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and AcOEt (20:1-3:1) to give 1-tert-butyl 5-ethyl 2-[(acetyloxy)acetyl]pentanedioate as yellow oil (4.27 g).

Workup

customThe mixture was partitioned between AcOEt and water
customThe organic layer was separated
washwashed with brine
dry with materialdried over MgSO4
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography
washeluting with a mixture of hexane and AcOEt (20:1-3:1)

Sources & evidence

ORD record: ord-d6b9ba51eb2544649fd3b323771b8747
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317009B2

Reaction notes

Loading…