Dimethylformamide → HCID 178515701, compound

HRID 2057568

Reaction equation

HRID 2057568 reaction equation
[CH:1]1[C:6]([O:7][C@@H:8]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]([OH:17])[C@H:9]2[OH:18])=[C:5]([OH:19])[CH:4]=[C:3]2[O:20][C:21]([CH:23]=[CH:24][C:2]=12)=[O:22].CN(C)C=O.ClC(OC)=O.[OH-].[Na+]>CC(C)=O>[CH:1]1[C:6]([O:7][C@@H:8]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]([OH:17])[C@H:9]2[OH:18])=[C:5]([OH:19])[CH:4]=[C:3]2[O:20][C:21]([CH:23]=[CH:24][C:2]=12)=[O:22].[CH2-:5][C:6]([CH3:1])=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 5281417Esculin

Product 1

HCID 178515701HCID 178515701, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 10 grams of esculin, 50 cc of dimethylformamide and 50 cc of acetone is cooled to 0° C. While maintaining the temperature at 0° C., 10 cc of methyl chloroformate are added dropwise. This procedure is repeated at the end of 3 hours. The mixture is kept overnight at ambient temperature with agitation. It is then cooled to 0° C. and neutralized with a minimum quantity of methanolic sodium hydroxide. The solvents are removed by evaporation and the residue is dissolved in water. The acetonide is extracted with ethyl acetate. The ethyl acetate extracts are dried and evaporated. The crude product is purified by column chromotography on polyamide SC6. The acetonide is then dried under vacuum at 100° C.

Workup

  1. customis repeated at the end of 3 hours
  2. temperatureIt is then cooled to 0° C.
  3. customThe solvents are removed by evaporation
  4. dissolutionthe residue is dissolved in water
  5. extractionThe acetonide is extracted with ethyl acetate
  6. dry with materialThe ethyl acetate extracts are dried
  7. customevaporated
  8. customThe crude product is purified by column chromotography on polyamide SC6
  9. dry with materialThe acetonide is then dried under vacuum at 100° C.

Sources & evidence

ORD record
ord-39b00e443303449cb16eda8f9c44ff99
Source dataset
uspto-grants-1980_07
Patent number
US04211772

Linked notes

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