Potassium Hydroxide → HCID 18549081, compound

HRID 842052Notes

Reaction equation

HRID 842052 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:10][CH:11]2[CH:15]([CH:16]=1)[CH2:14][C:13](=[O:17])[CH2:12]2)#[N:2].[OH-:18].[K+]>C(O)(C)(C)C>[O:17]=[C:13]1[CH2:12][CH:11]2[CH:15]([CH2:16][CH:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]([NH2:2])=[O:18])[CH2:10]2)[CH2:14]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 9920903HCID 9920903, compound

Product 1

HCID 18549081HCID 18549081, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

5-(2-Cyano-phenyl)-3,3a,4,6a-tetrahydro-1H-pentalen-2-one, ethylene ketal (0.25 g, 0.935 mmol) and powdered potassium hydroxide (0.5 g, 8.9 mmol) in t-butanol (5 mL0 were refluxed for 2 hours. After concentration, the reaction was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulfate and concentrated to give 0.296 g (111%) 2-(5-oxo-octahydro-pentalen-2-yl)-benzamide, ethylene ketal as light yellow oil which solidified upon standing. A portion was triturated with hexanes to give a dull yellow solid which had the following properties: mp 111-1 12.5° C.; NMR (CDCl3) δ 7.66 (dd, J1=7.5 Hz, J2=1.5 Hz, 1H), 7.36-7.18 (m, 3H), 6.56 (br s, 2H),5.71 (t, J=2.1 Hz, 1H), 3.88-3.82 (m, 4H), 3.44-3.33 (m, 1H), 3.03-2.87 (m, 2H), 2.63-2.49 (m, 1H), 2.11-1.93 (m, 2H), 1.78-1.67 (m, 2H); 13C NMR (CDCl3) δ 171.65, 141.48, 136.24, 134.20, 133.69, 130.33, 129.10, 128.96, 127.33, 118.19, 64.43, 64.11, 49.78, 43.68, 42.80, 39.83, 39.19; IR(KBr) 3386, 3171, 2967, 2940, 2897, 1666, 1387, 1325, 1111, 781, 771, 631; Anal. calculated for C17H13NO3: C, 71.56; H, 6.71; N, 4.91. Found: C, 71.39; H, 6.85; N, 4.92.

Workup

  1. concentrationAfter concentration
  2. customthe reaction was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c05b79e666c5435fae1d4ac71e916f70
Source dataset
uspto-grants-2002_04
Patent number
US06372762B1

Reaction notes

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