Acetic Acid → HCID 89924099, compound

To a stirred solution of 4,4-dimethyl-3-oxocyclopent-1-enecarbonitrile (Step 1, 6 g, 44.4 mmol) in methanol (50 ml) was added sodium borohydride (2.52 g, 66.6 mmol) at 0° C. under nitrogen atmosphere. Reaction mixture was stirred at same temperature for 20 mins. Progress of reaction was monitored by TLC. After completion of reaction, distilled the reaction mixture was concentrated under reduced pressure. To crude reaction mass water (10 ml) was added followed by addition of 1 ml acetic acid. Aqueous reaction mixture was extracted in ethyl acetate (2×25 ml). Combined organic layer was dried on sodium sulphate and concentrated under reduced pressure to get oily compound which was directly used for next reaction without further purification (3.9 g).

1. customReaction mixture
2. customProgress of reaction
3. customAfter completion of reaction
4. distillationdistilled the reaction mixture
5. concentrationwas concentrated under reduced pressure
6. customTo crude reaction mass water (10 ml)
7. additionwas added
8. extractionAqueous reaction mixture was extracted in ethyl acetate (2×25 ml)
9. customCombined organic layer was dried on sodium sulphate
10. concentrationconcentrated under reduced pressure
11. customto get oily compound which
12. customwas directly used for next reaction without further purification (3.9 g)

ORD record

ord-8519b37c1911449a9d055d208d987331

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359367B2