Acetic Acid → HCID 70043803, compound

HRID 36983Notes

Reaction equation

HRID 36983 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)/[C:12](OC)=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].C([Al+]CC(C)C)C(C)C.CO.C(O)(=O)C>O1CCCC1.Cl.O>[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)/[CH2:12][OH:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 11743343methyl (E) 3-[2-n-butyl-1-[(2-chlorophenyl)methyl]-1H-imidazol-5-yl]-(2-thienyl)methyl-2-propenoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 70043803HCID 70043803, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate, prepared in Example 1, ((2.60 g. 6.06 mmol) in 35 mL of tetrahydrofuran at -78° C. under argon was added a solution of diisobutylaluminum hydride (1.5M, 8.9 mL, 13.3 mmol). After the addition was complete, the reaction mixture was allowed to warm to room temperature, with stirring being continued for one hour. The reaction was worked up by the slow addition of methanol, followed by the addition of glacial acetic acid, then four drops of 10% aqueous hydrochloric acid solution. Water (10 mL) was added and the reaction mixture was stirred at room temperature overnight. The product was extracted with ethyl acetate (3×75 mL) after 40 mL of water had been added to the mixture. The combined extracts were dried with anhydrous magnesium sulfate and the solvents were removed in vacuo. The residue was triturated with diethyl ether. The resulting solid was filtered to give 1.72 g (71%) of product; mp 114°-115° C.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. extractionThe product was extracted with ethyl acetate (3×75 mL) after 40 mL of water
  4. additionhad been added to the mixture
  5. dry with materialThe combined extracts were dried with anhydrous magnesium sulfate
  6. customthe solvents were removed in vacuo
  7. customThe residue was triturated with diethyl ether
  8. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-bb3860a2d9424e079efe9caf62f4ae2c
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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