Diethyl Ether → HCID 21527738, compound

HRID 1658521Notes

Reaction equation

HRID 1658521 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.Cl.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH:30]3[C:31]([O:33][C:34](=O)[CH:29]3[CH:28]3[C:23]([CH2:24][CH2:25][N:26]([CH3:36])[CH2:27]3)=[CH:22]2)=[O:32])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]2[CH:30]([CH2:31][OH:32])[CH:29]([CH2:34][OH:33])[CH:28]3[C:23]([CH2:24][CH2:25][N:26]([CH3:36])[CH2:27]3)=[CH:22]2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 21226445Aluminium lithium hydrideHCID 86733572HCID 86733572, compound

Product 1

HCID 21527738HCID 21527738, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a slurry of 15 g lithium aluminum hydride in 800 ml. ether and 400 ml. dioxane is added 15 g (0.041 moles) 1,2,3,4,6,7,8,8a-octahydro-6-(p-methoxyphenyl)-2-methyl-7,8-isoquinoline-dicarboxylic acid anhydride hydrochloride slowly with stirring under nitrogen. This mixture is refluxed ovenight. Saturated potassium carbonate solution is added until the solution is white. This is filtered and washed with hot dioxane. The organics are combined and evaporated to yield 7.9 g (61%) crude 1,2,3,4,6,7,8,8a-octahydro-6-(p-methoxyphenyl)-2-methyl-7,8-isoquinolinedimethanol. The oil is crystallized from ethyl acetate, and recrystallization of 2 g from ethyl acetate gives an analytical sample, 1.7 g, mp 169°-171°C.

Workup

  1. temperatureThis mixture is refluxed ovenight
  2. filtrationThis is filtered
  3. washwashed with hot dioxane
  4. customevaporated

Sources & evidence

ORD record
ord-87cb607a7d0a403ea4a271f85b4d1e50
Source dataset
uspto-grants-1976_06
Patent number
US03965102

Reaction notes

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