Diisobutylaluminum hydride → HCID 53242308, compound

To a solution of ethyl 3-(4-cyanophenyl)propiolate (2.2 g, 11.04 mmol, 1.00 equiv) in dichloromethane (10 mL) maintained under nitrogen at −65° C. was added a 25% DIBAL (22 mL, 2.00 equiv) solution in toluene dropwise with stirring. The resulting solution was stirred at −65° C. for 2 h and then quenched by the addition of 5 mL of saturated sodium potassium tartrate solution. The solid material was removed by filtration. The filtrate was extracted with 3×30 mL of dichloromethane. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-10% of methanol in dichloromethane to give 627 mg (37%) of 4-(3-oxoprop-1-ynyl)benzonitrile as a white solid.

1. stirringThe resulting solution was stirred at −65° C. for 2 h
2. customquenched by the addition of 5 mL of saturated sodium potassium tartrate solution
3. customThe solid material was removed by filtration
4. extractionThe filtrate was extracted with 3×30 mL of dichloromethane
5. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum
7. customThe residue was purified on a silica gel column
8. washeluted with 0-10% of methanol in dichloromethane

ORD record

ord-0d6bbaf15bbb4e50a47403624543a164

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365527B2