Chloroform → HCID 19389477, compound

HRID 445902Notes

Reaction equation

HRID 445902 reaction equation
[C:1]([O:4][C:5]1[C:6](=[O:16])[O:7][C:8]([CH2:11][O:12][C:13](=[O:15])[CH3:14])=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(Cl)(Cl)Cl>C(OCC)(=O)C.[Pd]>[C:1]([O:4][CH:5]1[C:6](=[O:16])[O:7][CH:8]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH2:9][CH2:10]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 11264614HCID 11264614, compound

Product 1

HCID 19389477HCID 19389477, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

3-Acetoxy-6-acetoxymethyl-pyran-2-one (2.2) (4.80 g, 21.2 mmol) was dissolved in ethyl acetate (50 mL) and added to the Parr reactor, followed by Pd/C (5%, 0.2 g). The mixture was stirred under hydrogen (5×106 Pa) and heated to 75° C. for 4 hours. The product was filtered through celite and the solvent removed under vacuum. A colourless syrup was obtained (4.83 g, 21.0 mmol, 99%). 1H NMR (400 MHz, CDCl3) δ 5.45 (1H, dd, 3JH—H=17.08 Hz, 3JH—H=8.55 Hz, H-2), 4.65 (1H, m, H-5), 4.26 (1 H, dd, 2JH—H=12.13 Hz, 3JH—H=3.54 Hz, H-6), 4.18 (1 H, dd, 2JH—H=12.16, 3JH—H=6.32 Hz, H-6′), 2.36 (1H, m, H-3), 2.19 (3H, s, COCH3), 2.11 (3H, s, COCH3), 2.07-1.88 (3H, m, H-3′, H-4, H-4′) ppm. 13C{1H} NMR (125 MHz, CDCl3) δ 170.6, 169.8, 168.6 (2×COCH3, C-1), 74.9 (C-5), 65.9 (C-2), 64.9 (C-6), 22.7, 22.4 (C-3, C-4), 20.7 (2×COCH3) ppm. CI (NH4+): 248 (100%), 306 (30%), 478 (20%). m/z (CI-ammonia gas): 248 [M+NH4+]. [α]D=0° (CHCl3, 10 mg/mL). Anal. Calcd for C10H14O6: C, 52.17; H, 6.13. Found: C, 52.11; H, 6.17.

Workup

  1. additionadded to the Parr reactor
  2. filtrationThe product was filtered through celite
  3. customthe solvent removed under vacuum
  4. customA colourless syrup was obtained (4.83 g, 21.0 mmol, 99%)

Sources & evidence

ORD record
ord-abdd351d49d147498db96a63e2111599
Source dataset
uspto-grants-2013_07
Patent number
US08476402B2

Reaction notes

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