Ethyl Acetate → HCID 68500659, compound

HRID 1176557Notes

Reaction equation

HRID 1176557 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:26]1[C:30]2[C:31]([C:35](OC)=[O:36])=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].C(OCC)(=O)C>O1CCCC1>[C:7]([N:26]1[C:30]2[C:31]([CH2:35][OH:36])=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 68500922HCID 68500922, compound

Product 1

HCID 68500659HCID 68500659, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 0.210 g of lithium aluminium hydride in 15 ml of anhydrous tetrahydrofuran is cooled under argon to 0° C. A solution of 2.300 g of methyl 3-trityl-3H-benzimidazole-4-carboxylate in 25 ml of anhydrous tetrahydrofuran is added dropwise to the suspension over 5 minutes and the reaction mixture is subsequently stirred at 0° C. over one hour. The reaction mixture is subsequently poured slowly onto 80 ml of 1M sodium potassium tartrate solution and admixed with ethyl acetate (100 ml). The phases are separated and the aqueous phase is extracted with (100 ml)of ethyl acetate. The combined organic phases are washed with 100 ml of water, dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a reddish foam and is used for the next stage without further purification. Rt=4.04.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted with (100 ml)of ethyl acetate
  3. washThe combined organic phases are washed with 100 ml of water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d8eb0b6ca86245c28eb529056f0f2cba
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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