Dichloromethane → HCID 23311327, compound

HRID 746055Notes

Reaction equation

HRID 746055 reaction equation
[O:1]=[C:2]1[C:6]([CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[CH:5]2[CH2:19][CH:20]=[CH:21][CH:22]=[C:4]2[O:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(Cl)[Cl:30]>C1COCC1>[ClH:30].[CH3:18][N:16]([CH3:17])[CH2:15][CH2:14][C:6]([C:5]1[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=1[OH:3])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[CH2:2][OH:1]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 21226445Aluminium lithium hydrideHCID 53787862HCID 53787862, compound

Product 1

HCID 23311327HCID 23311327, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[2-oxo-3-(2-tolyl)-3-dihydrobenzofuranyl]-N,N-dimethylethylamine (90 g, 305 mmol) in anhydrous THF (400 ml) was added to a suspension of LiAlH4 (11.4 g, 300 mmol) in THF (850 ml) at 0°. This mixture was stirred 1 hour, quenched with saturated NH4Cl (200 ml) and the organic phase decanted. The solids were washed with EtOAc (3×300 ml) and decanted. The organic solutions were combined and evaporated in vacuo to give an oil which solidified on cooling. The crude residue was dissolved in CH2Cl2 (500 ml), washed with dilute NH4Cl until the pH became 8, and dried over Na2SO4. A solution of the diolamine (8.4 g) in CH2Cl2 (60 ml) was added dropwise to an ethereal/HCl solution (1200 ml). Filtration of the precipitated salt gave 8.6 g of a solid, which was recrystallized from MeCN (800 ml) to yield 6.7 g (71%) of crystals, m.p. 205°-207°.

Workup

  1. customquenched with saturated NH4Cl (200 ml)
  2. customthe organic phase decanted
  3. washThe solids were washed with EtOAc (3×300 ml)
  4. customdecanted
  5. customevaporated in vacuo
  6. customto give an oil which
  7. temperatureon cooling
  8. washwashed with dilute NH4Cl until the pH
  9. dry with materialdried over Na2SO4
  10. additionA solution of the diolamine (8.4 g) in CH2Cl2 (60 ml) was added dropwise to an ethereal/HCl solution (1200 ml)
  11. filtrationFiltration of the precipitated salt

Sources & evidence

ORD record
ord-1d8b487eb3284a0aab6ab386f5c75cfe
Source dataset
uspto-grants-1986_07
Patent number
US04602035

Reaction notes

Loading…