Aluminium lithium hydride → HCID 59070242, compound

HRID 1813947Notes

Reaction equation

HRID 1813947 reaction equation
C([O:3][C:4](=O)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:15][CH2:16][Cl:17])=[CH:9][CH:8]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:17][CH2:16][CH2:15]/[C:14](/[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[C:13](/[C:10]1[CH:9]=[CH:8][C:7]([NH:6][CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1)\[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69544455HCID 69544455, compound

Product 1

HCID 59070242HCID 59070242, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)phenylamino]acetic acid ethyl ester (2.9 g, 6.9 mmol) is dissolved in tetrahydrofuran and lithium aluminum hydride (0.34 g, 8.97 mmol) is added in small portions during fifteen minutes. The mixture is stirred at room temperature for two hours. Then the solvent is evaporated to dryness and the residue is dissolved in ethyl acetate and washed with water. Ethyl acetate phase is evaporated to dryness and the product is purified by flash chromatography with toluene:methanol:triethylamine solution (10:0.3:0.3) as an eluent. Yield 0.47 g.

Workup

  1. customThen the solvent is evaporated to dryness
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with water
  4. customEthyl acetate phase is evaporated to dryness
  5. customthe product is purified by flash chromatography with toluene

Sources & evidence

ORD record
ord-1a10d2ec88214439bd2c78b301d51508
Source dataset
uspto-grants-2005_04
Patent number
US06875775B2

Reaction notes

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