Formaldehyde → 3-(4-Carbethoxyphenyl)-5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-oxazolidine

HRID 1591127Notes

Reaction equation

HRID 1591127 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH:14]([C:16]2[CH:25]=[CH:24][C:23]3[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]([CH3:29])([CH3:28])[C:18]=3[CH:17]=2)[OH:15])=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].P([O-])([O-])O.[Na+].[Na+].[CH2:36]=O>O1CCOCC1>[C:1]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:13][CH:14]([C:16]3[CH:25]=[CH:24][C:23]4[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]([CH3:28])([CH3:29])[C:18]=4[CH:17]=3)[O:15][CH2:36]2)=[CH:10][CH:11]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14726540N-(4-carbethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-aminoethanolHCID 177427533Disodium;hydrogen phosphite

Product 1

HCID 147265413-(4-Carbethoxyphenyl)-5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-oxazolidineYield 61.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.58 g (4 millimoles) of N-(4-carbethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-aminoethanol were stirred with 20 ml of 1N sodium hydrogen phosphite solution and 2 ml (20 millimoles) of formalin solution in 20 ml of dioxane for 1 hour at 60° C. The mixture was then poured onto water and extracted with ether, and the organic phase was washed with 2N sodium hydroxide solution and water, dried over magnesium sulfate and evaporated down. Recrystallization from methanol gave 1.0 g of the title compound, Rf =0.51 (thin layer chromatography, silica gel; 7:1 n-heptane/ethyl acetate).

Workup

  1. additionThe mixture was then poured onto water
  2. extractionextracted with ether
  3. washthe organic phase was washed with 2N sodium hydroxide solution and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-ec6bd5500a574049afdb562dd4256722
Source dataset
uspto-grants-1993_04
Patent number
US05206242

Reaction notes

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