Chloroform → HCID 13020713, compound

HRID 1680678Notes

Reaction equation

HRID 1680678 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:11][C@:12]12[O:36][C@H:13]1[C@@H:14]1[O:35][C:17]3=[C:18]([O:33][CH3:34])[CH:19]=[CH:20][C:21]4[C:22](=C)[C@H:23]5[N:28]([CH3:31])[CH2:29][CH2:30][C@:15]1([C@H:24]5[C@H:25]2[CH2:26][CH3:27])[C:16]=43.[CH:37](Cl)(Cl)Cl>CCOCC.C(Cl)(Cl)Cl.CCCCCC>[O:35]1[C@@H:14]2[C@@:15]34[CH2:30][CH2:29][N:28]([CH3:31])[C@@H:23]([C@@H:24]3[C@@H:25]([CH2:26][CH3:27])[C:12]([CH3:37])([CH3:11])[C@H:13]2[OH:36])[CH2:22][C:21]2=[C:16]4[C:17]1=[C:18]([O:33][CH3:34])[CH:19]=[CH:20]2

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 86737816HCID 86737816, compound

Product 1

HCID 13020713HCID 13020713, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 21585165Chloroform hexaneSolvent

Procedure

A mixture of AlCl3 (8.0 g, 60 mmole) and LiAlH4 (6.8 g, 180 mmole) was prepared in Et2O (600 ml) as described above. To this was added 5c (21.3 g, 60 mmole) in Et2O (1 L) and the mixture refluxed for 36 hours. Processing as described gave a foam. Crystals of 6c (10.0 g) as the CHCl3 solvate, mp 104°-108°, were obtained from CHCl3 -hexane. An additional 2.7 g of 6c (50% overall yield) was obtained by processing the mother liquor.

Workup

  1. temperaturethe mixture refluxed for 36 hours
  2. customProcessing as described gave a foam

Sources & evidence

ORD record
ord-976d795bb88d4985b809eb00d06cd75f
Source dataset
uspto-grants-1981_06
Patent number
US04275205

Reaction notes

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