Methanol → HCID 54492923, compound

HRID 436523Notes

Reaction equation

HRID 436523 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[O:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1.[BH4-].[Na+].[CH3:21]O.[C:23](=[O:26])([O-])[O-].[K+].[K+]>C(O)C.O>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[O:12][C:13]([CH2:16][O:17][C:23](=[O:26])[CH3:21])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 15841978HCID 15841978, compound

Product 1

HCID 54492923HCID 54492923, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

8.22 g of 8-(5-formyl-2-furyl)-octanoic acid methyl ester were dissolved in 100 ml of absolute ethanol, whereupon the solution was cooled to 10° C. 5.0 g. of sodium borohydride (98%) in 100 ml of ethanol were added in one portion while stirring. After 1.5 hours, 10 ml of methanol were added and the solution poured into 150 ml of water. 50 g of potassium carbonate were then added, the temperature being kept below 18° C. The solution was then extracted several times with ether while adding further quantities of potassium carbonate. After drying, the ether was driven off. 10 ml of pyridine were then added to the product, after which the mixture was again dried. The residue was dissolved in 65 ml of pyridine, after which 65 ml of acetic anhydride were added. The mixture was allowed to stand overnight and was then distilled under vacuum. A product having a boiling point of 148°-149° C at 0.2 mm Hg was obtained.

Workup

  1. custombeing kept below 18° C
  2. extractionThe solution was then extracted several times with ether
  3. additionwhile adding further quantities of potassium carbonate
  4. customAfter drying
  5. addition10 ml of pyridine were then added to the product
  6. customafter which the mixture was again dried
  7. dissolutionThe residue was dissolved in 65 ml of pyridine
  8. additionafter which 65 ml of acetic anhydride were added
  9. waitto stand overnight
  10. distillationwas then distilled under vacuum
  11. customwas obtained

Sources & evidence

ORD record
ord-f708a972cf5845948df97fb16a8bcae5
Source dataset
uspto-grants-1977_02
Patent number
US04009187

Reaction notes

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