Potassium Cyanide → HCID 66652174, compound

HRID 418962Notes

Reaction equation

HRID 418962 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]([OH:13])[CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[CH:7]1[CH2:16][CH2:15][CH2:14][CH:8]12.[C-:24]#[N:25].[K+].C1OCCOCCOCCOCCOCCOC1>>[OH:13][C:11]1[CH:10]=[C:9]2[C:4]([CH2:5][CH:6]([C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=3)[CH:7]3[CH2:16][CH2:15][CH2:14][CH:8]32)=[C:3]([CH2:2][C:24]#[N:25])[CH:12]=1

Participants

4

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 66652223HCID 66652223, compound

Product 1

HCID 66652174HCID 66652174, compound

Procedure

Combine 6-Bromomethyl-4-(4-hydroxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-8-ol (0.037 g, 0.1 mmol), KCN (0.010 g, 0.15 mmol), and 18-crown-6 (0.043 g, 0.16 mmol) and heat at 80° C. for 2 hours. Cool, add ice and extract with ethyl acetate. Wash organic layer with sodium bicarbonate solution sat., then water. Dry over anhydrous sodium sulfate and concentrate to a residue which yields, after separation on silica gel with 33% EtOAC/hexanes, the titled compound (0.022 g, 70%). 1H NMR (DMSO-d6) 9.27(s, 1H), 9.18 (s, 1H), 7.13 (d, J=8.4 Hz, 2H), 6.73 (d, J=7.9 Hz, 2H), 6.66 (s, 1H), 6.59 (s, 1H), 3.95 (s, 2H), 3.4 (m, 1H presumed), 3.0 (m, 1H), 2.76 (m, 1H), 2.65 (m, 1H), 2.45(m, 1H) 2.15 (m, 1H), 1.6-1.2 (m, 5H). MS m/z 318 (M−1).

Workup

  1. temperatureCool
  2. additionadd ice
  3. extractionextract with ethyl acetate
  4. dry with materialDry over anhydrous sodium sulfate
  5. concentrationconcentrate to a residue which
  6. customyields
  7. customafter separation on silica gel with 33% EtOAC/hexanes

Sources & evidence

ORD record
ord-a15f618b811d49caa86177516eb10eb8
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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