Methanol → HCID 19384564, compound

HRID 2399809Notes

Reaction equation

HRID 2399809 reaction equation
[CH2:1]([CH:9]1[C:14]2=[C:15]3[CH2:21][CH2:20][CH2:19][CH2:18][C:16]3=[N:17][C:13]2=[C:12]([C:22]([C:24]2[O:28][C:27]([CH:29]=[O:30])=[CH:26][CH:25]=2)=[O:23])[CH:11]=[CH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:31]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:42][OH:43]>>[CH3:42][O:43][CH:29]([O:30][CH3:31])[C:27]1[O:28][C:24]([C:22]([C:12]2[CH:11]=[CH:10][CH:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:14]3[C:13]=2[N:17]=[C:16]2[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=32)=[O:23])=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 19384475HCID 19384475, compound

Product 1

HCID 19384564HCID 19384564, compound

Procedure

A mixture of 11.2 g of aldehyde from Example 155, and 1.0 g of p-toluenesulfonic acid in 150 mL of methanol was refluxed for 2 hours. After evaporation of the solvent the residue was poured into a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The material obtained as an orange-brown oil (11.9 g; 95%) was used without further purification.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter evaporation of the solvent the residue
  3. additionwas poured into a saturated solution of sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. customThe material obtained as an orange-brown oil (11.9 g; 95%)
  6. customwas used without further purification

Sources & evidence

ORD record
ord-14a5291cd1de4153a0d659946a7cf927
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

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