Chloroform → HCID 13034463, compound

HRID 1759241Notes

Reaction equation

HRID 1759241 reaction equation
[C:1]([C:5]1[C:6](=[O:21])[CH2:7][CH2:8][N:9]2[C:14]=1[CH2:13][CH2:12][CH:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10]2)([O:3][CH3:4])=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.C(Cl)(Cl)Cl>CCOCC>[C:1]([CH:5]1[CH:14]2[N:9]([CH2:10][CH:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)[CH2:8][CH2:7][C:6]1=[O:21])([O:3][CH3:4])=[O:2]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8028TetrahydrofuranHCID 13034462HCID 13034462, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13034463HCID 13034463, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound I (15.1 g.) was suspended in ether and LiAlH4 (1.5 g.; 0.75 equiv.) was added portionwise at room temperature. The mixture was stirred for 1 hr. at room temperature. The mixture was treated with wet THF and the mixture filtered. The filtrate was treated with CHCl3 /H2O, the CHCl3 separated, dried and the solvent removed in vacuo. Yield, 9 g. The filter-cake was stirred repeatedly with CHCl3 and an additional 4.1 g. of material was obtained. The 13.1 g. was chromatographed on a silica gel column. Compound II was eluted with CHCl3. Yield, 6.82 g. (44.9% yield).

Workup

  1. customat room temperature
  2. filtrationthe mixture filtered
  3. additionThe filtrate was treated with CHCl3 /H2O
  4. customthe CHCl3 separated
  5. customdried
  6. customthe solvent removed in vacuo
  7. customYield
  8. customof material was obtained
  9. customwas chromatographed on a silica gel column
  10. washCompound II was eluted with CHCl3
  11. customYield

Sources & evidence

ORD record
ord-296b9c4e3cba41429d86b16de48d8aac
Source dataset
uspto-grants-1982_07
Patent number
US04339582

Reaction notes

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