HCID 67688146, compound → HCID 67688172, compound

HRID 2257233Notes

Reaction equation

HRID 2257233 reaction equation
C([O:8][C:9]1[C:10](=[O:33])[O:11][C@@H:12]([CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:13]=1[OH:14])C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[C:10](=[O:33])[O:11][C@@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:13]=1[OH:14]

Participants

4

Reactant 1

HCID 67688146HCID 67688146, compound

Product 1

HCID 67688172HCID 67688172, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a 250 mL hydrogenation bottle was added 0.02 g of 10% palladium on carbon in 5 mL methanol. To this suspension was added 0.1 g (0,219 mmol) of (S)-3-benzyloxy-4-hydroxy-5-[(Z)-3-octadecenyl]-2(5H)-furanone dissolved in 15 mL methanol. Hydrogenation was initiated at 40 psi and at room temperature. The reaction was monitored for completion by TLC (approximately 5-6 hours), filtered (Celite) and evaporated under reduced pressure. The residue was purified over silica gel using 10% methanol in chloroform as eluant to generate 58 mg (72%) of white solid: mp 110°-112° C.; [α]D25 -6.8° (c=0.3, CH3OH); IR (Kbr, cm-1) 3380 (br), 2917, 2848, 1741, 1668; 1H NMR (CD3COCD3) δ 4.67 (dd, J=3.5, 7.3 Hz, 1H), 2.01-1.88 (m, 1H), 1.57-1.47 (m, 1H), 1.42-1.23 (m, 322), 0.87 (t, J=6.8 Hz, 3H); HRMS calculated for C22H40O4 (M+), 368.2927, found 368.2928; analysis calculated for C22H40O4 +0.5 H2O: C, 69.99; H, 10.95; Found: C, 70.27; H, 11.22.

Workup

  1. customwas initiated at 40 psi and at room temperature
  2. customwas monitored for completion by TLC (approximately 5-6 hours)
  3. filtrationfiltered (Celite)
  4. customevaporated under reduced pressure
  5. customThe residue was purified over silica gel using 10% methanol in chloroform as eluant

Sources & evidence

ORD record
ord-537e9f4207564ca89f4a1e8f9dc43e86
Source dataset
uspto-grants-1997_08
Patent number
US05656662

Reaction notes

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