Dichloromethane → HCID 23311355, compound

HRID 746053Notes

Reaction equation

HRID 746053 reaction equation
[O:1]=[C:2]1[C:6]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]2[CH2:18][CH:19]=[CH:20][CH:21]=[C:4]2[O:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(Cl)[Cl:29].CCOCC.Cl>CCOCC>[ClH:29].[CH3:17][N:15]([CH3:16])[CH2:14][CH2:13][C:6]([C:5]1[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=1[OH:3])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][OH:1]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10953452Ether hydrochlorideHCID 21226445Aluminium lithium hydrideHCID 53792328HCID 53792328, compound

Product 1

HCID 23311355HCID 23311355, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 28.6 g (102 mmole) 2-(2-oxo-3-phenyl-3-dihydrobenzofuranyl)-N,N-dimethylethylamine in 300 ml anhydrous Et2O was added to 7.74 g (204 mmole) LiAlH4 in 150 ml Et2O at ice bath temperature and this mixture stirred at that temperature for 30 minutes. After further stirring for 2 hours at room temperature, the reaction mixture was quenched with saturated Na2SO4, filtered, and the solids washed with excess EtOAc (4×350 ml). The combined organics were washed with saturated Na2CO3 (300 ml) and saturated NaCl (200 ml), and dried over Na2SO4. Filtration and evaporation gave 28 g of a crude oil which solidified on standing. A solution of 5 g of this material in a minimum amount of CH2Cl2 was added to excess Et2O/HCl. Filtration of the precipitated salt gave 5.5 g of a solid which was recrystallized from EtOH to give 3.2 g (57%) of crystals, m.p. 199°-201°.

Workup

  1. stirringAfter further stirring for 2 hours at room temperature
  2. customthe reaction mixture was quenched with saturated Na2SO4
  3. filtrationfiltered
  4. washthe solids washed with excess EtOAc (4×350 ml)
  5. washThe combined organics were washed with saturated Na2CO3 (300 ml) and saturated NaCl (200 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and evaporation
  8. customgave 28 g of a crude oil which
  9. filtrationFiltration of the precipitated salt

Sources & evidence

ORD record
ord-9e44465b8d7b4866b9ac89143fffe1a1
Source dataset
uspto-grants-1986_07
Patent number
US04602035

Reaction notes

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