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

HRID 1614399Notes

Reaction equation

HRID 1614399 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 1 N 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 2 N 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 2 N sodium hydroxide solution and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-09a7412eb8a74267a49fa51df8651f36
Source dataset
uspto-grants-1993_03
Patent number
US05196532

Reaction notes

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