HCID 18956332, compound → HCID 18956329, compound

HRID 2379899Notes

Reaction equation

HRID 2379899 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH:19]([CH3:21])[CH3:20])(OCC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:2][CH2:1][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH:19]([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 18956332HCID 18956332, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18956329HCID 18956329, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Part B. A solution of the ester obtained in Part A above (9.54 g, 33.1 mmol) in tetrahydrofuran (30 mL) was added to a solution of lithium aluminum hydride (80 mmol) in tetrahydrofuran (80 mL) at 0° C. The mixture was heated to reflux overnight, then cooled back to 0° C. and quenched by the careful sequential addition of water (3 mL), then aqueous sodium hydroxide solution (10 mL of 15%), then water (10 mL). The mixture was filtered through celite with copius tetrahydrofuran washing, and the liquid was dried over anhydrous potassium carbonate, filtered and evaporated. The residual oil was separated by flash chromatography (ethyl acetate) to afford the product, 1-(5-hydroxypentyl)-2-(1-methylethyl)-1H-benzimidazole (6.82 g, 27.7 mmol, 84%) as an oil. 1H NMR (CDCl3) : 7.78-7.70 (1H, m); 7.32-7.22 (3H, m); 4.90 (1H, br d, J=2.2 Hz); 4.12 (2H, t, J=7.5 Hz); 3.64 (2H, t, J=6.0 Hz); 3.18 (1H, m, J=6.6 Hz); 1.93-1.45 (6H, m); 1.44 (6H, d, J=6.6 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customquenched by the careful sequential addition of water (3 mL)
  4. filtrationThe mixture was filtered through celite with copius tetrahydrofuran washing
  5. dry with materialthe liquid was dried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual oil was separated by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-5f793ef5eb294aa59b402e6614abef7b
Source dataset
uspto-grants-1994_11
Patent number
US05364875

Reaction notes

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