Water → [5-(4-Ethoxy-2,3-difluorophenyl)selenophen-2-yl]methanol

HRID 1873407Notes

Reaction equation

HRID 1873407 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[Se:14][C:13]([CH:15]=[O:16])=[CH:12][CH:11]=2)=[C:6]([F:17])[C:5]=1[F:18])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[H][H]>C(OCC)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[Se:14][C:13]([CH2:15][OH:16])=[CH:12][CH:11]=2)=[C:6]([F:17])[C:5]=1[F:18])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 594563155-(4-Ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 59456265[5-(4-Ethoxy-2,3-difluorophenyl)selenophen-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3.9 g (12.4 mmol) of 5-(4-ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde as a suspension in 100 ml of diethyl ether are added slowly to a suspension of 0.47 g (12.4 mmol) of lithium aluminium hydride in 20 ml of diethyl ether with ice-cooling. When the addition is complete, the mixture is stirred for 5 min, and water is added dropwise to the mixture until evolution of hydrogen no longer occurs. The mixture is filtered through Celite with MTBE. The filtrate is washed with water and dried using sodium sulfate. The solution is concentrated to dryness, and the crude product (yellowish crystals) is used directly for the subsequent reaction.

Workup

  1. temperaturecooling
  2. additionWhen the addition
  3. filtrationThe mixture is filtered through Celite with MTBE
  4. washThe filtrate is washed with water
  5. customdried
  6. concentrationThe solution is concentrated to dryness
  7. customthe crude product (yellowish crystals) is used directly for the subsequent reaction

Sources & evidence

ORD record
ord-609f5f57e7cf4f1d828e7d8fce02ddfa
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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