HCID 22789905, compound → HCID 22789921, compound

HRID 1287543Notes

Reaction equation

HRID 1287543 reaction equation
C([O:8][C:9](=[O:23])[C@H:10]([O:15][C:16]([C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1.[H][H]>[Pd]>[O:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[C:16]([O:15][C@H:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:9]([OH:23])=[O:8])=[O:17]

Participants

4

Reactant 2

HCID 22789905HCID 22789905, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22789921HCID 22789921, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A total of 55.5 g. of benzyl-(R)-2-(2-furoyloxy)-isocaproate were hydrogenated in 400 ml. of alcohol after the addition of 5 g. of palladium-on-charcoal (5 percent) until the theoretical amount of hydrogen had been taken up. The catalyst was filtered off by suction and the filtrate evaporated under reduced pressure at 40°. The oil thus obtained was dissolved in 250 ml. of 8 percent sodium bicarbonate solution and the resulting solution washed twice with 80 ml. portions of ether. The pH of the bicarbonate solution was adjusted to pH 2 with concentrated hydrochloric acid and extracted three times with 100 ml. portions of ethyl acetate. The ethyl acetate solutions were washed twice with 50 ml. portions of water, dried with magnesium sulphate and evaporated under reduced pressure at 45°. The residual oil was dried for 2 hours at 0.4 Torr and 40° to give (R)-2-(2-furoyloxy)-isocaproic acid; [α]D25 = + 7.0 (c = 4.0 in alcohol).

Workup

  1. filtrationThe catalyst was filtered off by suction
  2. customthe filtrate evaporated under reduced pressure at 40°
  3. customThe oil thus obtained
  4. dissolutionwas dissolved in 250 ml
  5. washof 8 percent sodium bicarbonate solution and the resulting solution washed twice with 80 ml
  6. extractionextracted three times with 100 ml
  7. washThe ethyl acetate solutions were washed twice with 50 ml
  8. dry with materialportions of water, dried with magnesium sulphate
  9. customevaporated under reduced pressure at 45°
  10. customThe residual oil was dried for 2 hours at 0.4 Torr and 40°

Sources & evidence

ORD record
ord-89fec97c270d4ce985d2bc07070ec420
Source dataset
uspto-grants-1976_10
Patent number
USRE029003

Reaction notes

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