HCID 19815307, compound → HCID 19815367, compound

HRID 653925Notes

Reaction equation

HRID 653925 reaction equation
[CH2:1]([O:8][C:9]1[CH:29]=[CH:28][C:12]([CH2:13][N:14]2[C:18]([C:19](OCC)=[O:20])=[CH:17][N:16]=[C:15]2[S:24][CH2:25][CH2:26][CH3:27])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:29]=[CH:28][C:12]([CH2:13][N:14]2[C:18]([CH2:19][OH:20])=[CH:17][N:16]=[C:15]2[S:24][CH2:25][CH2:26][CH3:27])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 19815307HCID 19815307, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19815367HCID 19815367, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.05 g of 1-(4-benzyloxybenzyl)-2-propylthio-5-carboethoxyimidazole in 10 mL of tetrahydrofuran was added dropwise to 10 mL of 1M lithium aluminum hydride in THF at 0° such that the reaction temperature remained below 5°. The resulting solution then was stirred at 0° for 1 hour. At this point, the reaction mixture was quenched by sequential dropwise addition of 0.40 mL of water, 0.40 mL of 15% aqueous sodium hydride, and 1.20 mL of water. The resulting suspension was filtered employing diethyl ether, and the filtrate was concentrated to furnish 1.55 g of 1-(4-benzyloxybenzyl)-2-propylthio-5-hydroxymethylimidazole; NMR (200 MHz, CDCl3): δ 7.41-7.29 (s, 5H); imidazole; NMR (200 MHz, CDCl3): δ 7.41-7.29 (s, 5H); 7.03-6.86 (m, 5H); 5.22 (s, 2H); 5.01 (s, 2H); 4.45 (s, 2H); 3.01 (t, 2H); 2.32 (bs, 1h); 1.66 (sext., 2H); 0.97 (t, 3H).

Workup

  1. customremained below 5°
  2. customAt this point, the reaction mixture was quenched by sequential dropwise addition of 0.40 mL of water, 0.40 mL of 15% aqueous sodium hydride, and 1.20 mL of water
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-230cf74279b646508cca9deb08ad7e90
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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