Acetone → 7-(1-methylethylidene)-1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one

HRID 2389901Notes

Reaction equation

HRID 2389901 reaction equation
[CH2:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]3[CH2:12][CH2:11][C:10](=[O:13])[C:8]3=2)[O:3][CH2:2]1.[CH3:14][C:15]([CH3:17])=O.IC#N>O1CCCC1>[CH3:14][C:15](=[C:11]1[C:10](=[O:13])[C:8]2=[C:9]3[CH2:1][CH2:2][O:3][C:4]3=[N:5][CH:6]=[C:7]2[CH2:12]1)[CH3:17]

Participants

5

Reactant 3

HCID 180Acetone2×HCID 10478Cyanogen iodideHCID 591793681,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one

Product 1

HCID 591794017-(1-methylethylidene)-1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-oneYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,2,6,7-Tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one (610 mg, 3.48 mmol), acetone (1.28 mL, 17.4 mmol) and ICN Alumina B (manufactured by ICN, Akt. 1, 10 g) were suspended in tetrahydrofuran (15 mL), and the suspension was stirred at room temperature for 3 hr. Acetone (1.28 mL, 17.4 mmol) was added, and the mixture was further stirred for 3 hr. The reaction solution was filtered, and the filtrate was evaporated under reduced pressure to give the title compound (539 mg, yield 72%).

Workup

  1. stirringthe mixture was further stirred for 3 hr
  2. filtrationThe reaction solution was filtered
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-43d626a53129413eabd316c960c677d8
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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