3-Phenylprop-2-Enal → HCID 11226026, compound

HRID 2181423Notes

Reaction equation

HRID 2181423 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7](=[O:16])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:17]([O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:38])=[CH:33][CH:32]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[CH2:17]([O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)([OH:38])[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][OH:16])=[CH:35][CH:36]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 11417531{4-[2-(2-Benzyloxyethoxy)ethoxy]phenyl}-phenyl-methanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 11226026HCID 11226026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

Lithium aluminum hydride (1.08 g, 28.6 mmol) is added into dry tetrahydrofuran (60 ml) under nitrogen atmosphere. Cinnamaldehyde (6.65 g, 50 mmol) in dry tetrahydrofuran (16 ml) is added at 24-28° C. The reaction mixture is stirred at ambient temperature for 1 h. {4-[2-(2-Benzyloxyethoxy)ethoxy]phenyl}-phenyl-methanone (14.0 g, 37 mmol) in dry tetrahydrofuran (16 ml) is added at 50-55° C. The reaction mixture is stirred at 60° C. for 3 h. Most of tetrahydrofuran is evaporated. Toluene (70 ml) and 2 M aqueous hydrogen chloride (50 ml) are added. The mixture is stirred for 5 min and the aqueous layer is separated and extracted with toluene (30 ml). The toluene layers are combined and washed with 2M HCl and water, dried and evaporated. The product is crystallized from isopropanol as a mixture of stereoisomers (8.8 g, 50%).

Workup

  1. additionis added at 50-55° C
  2. customMost of tetrahydrofuran is evaporated
  3. additionToluene (70 ml) and 2 M aqueous hydrogen chloride (50 ml) are added
  4. stirringThe mixture is stirred for 5 min
  5. customthe aqueous layer is separated
  6. extractionextracted with toluene (30 ml)
  7. washwashed with 2M HCl and water
  8. customdried
  9. customevaporated
  10. customThe product is crystallized from isopropanol as a mixture of stereoisomers (8.8 g, 50%)

Sources & evidence

ORD record
ord-0271116caf1348409aa2a7cc1c3460bb
Source dataset
uspto-grants-2005_05
Patent number
US06891070B2

Reaction notes

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