Potassium Cyanide → HCID 86645814, compound

HRID 386444Notes

Reaction equation

HRID 386444 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:19]#[N:20].[K+]>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH:17]([OH:18])[C:19]#[N:20])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 563558HCID 563558, compound

Product 1

HCID 86645814HCID 86645814, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-(4-(benzyloxy)phenyl)propanal (S49, 700 mg, 3.07 mmol, 1 equiv) in THF (13 mL) and H2O (18 mL) was treated with KCN (2.30 g, 35.3 mmol, 11.5 equiv). After stirring for 50 h at 25° C., the reaction was quenched with H2O and extracted with ether. The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated to afford S50 (755 mg, 2.96 mmol, 96%) as a white solid: 1H NMR (CDCl3, 400 MHz) 7.47-7.33 (m, 5H), 7.14 (d, 2H, J=8.8 Hz), 6.95 (d, 2H, J=8.8 Hz), 5.06 (s, 2H), 4.39 (t, 1H, J=6.9 Hz), 2.82-2.77 (m, 2H), 2.17-2.10 (m, 2H); 13C NMR (CDCl3, 100 MHz) 157.3, 136.9, 131.9, 129.4, 128.5, 127.9, 127.4, 119.9, 115.0, 70.0, 60.2, 36.6, 29.7; IR (film) νmax 3444, 2927, 2865, 2250, 1611, 1583, 1514, 1454, 1382, 1246, 1177, 1079, 1024, 912, 830, 738, 695 cm−1.

Workup

  1. customthe reaction was quenched with H2O
  2. extractionextracted with ether
  3. washThe organic layer was washed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford S50 (755 mg, 2.96 mmol, 96%) as a white solid

Sources & evidence

ORD record
ord-e8007cb503274d678bd94d01e5e33a6e
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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