Sulfuric Acid → 1-[(2S,4R)-4,5-diacetoxytetrahydrofuran-2-yl]propyl benzoate

HRID 60730Notes

Reaction equation

HRID 60730 reaction equation
[C:1]([O:9][CH:10]([C@H:13]1[O:22][C@@H:16]2[O:17][C:18]([CH3:21])(C)[O:19][C@@H:15]2[CH2:14]1)[CH2:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:26]C(=O)C)(=[O:25])[CH3:24].S(=O)(=O)(O)O>C(O)(=O)C.C(Cl)(Cl)Cl.CCOC(C)=O>[C:1]([O:9][CH:10]([C@@H:13]1[CH2:14][C@@H:15]([O:19][C:18](=[O:17])[CH3:21])[CH:16]([O:26][C:23](=[O:25])[CH3:24])[O:22]1)[CH2:11][CH3:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 1213963901-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propyl benzoate2×

Product 1

HCID 1213962911-[(2S,4R)-4,5-diacetoxytetrahydrofuran-2-yl]propyl benzoate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propyl benzoate (compound 26a, 6.73 g, 22.0 mmol) and acetic anhydride (11 mL) in acetic acid (44 mL) and chloroform (11 mL) was added concentrated sulfuric acid (200 uL) dropwise. After being stirred at room temperature overnight, the resulted mixture was diluted with EtOAc (100 mL) and washed with a saturated aqueous solution of NaHCO3 (100 mL) three times. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:20 to 1:10 EtOAc in petroleum ether) to afford 5.1 g 1-[(2S,4R)-4,5-diacetoxytetrahydrofuran-2-yl]propyl benzoate (compound 26b) as a viscous oil.

Workup

  1. washwashed with a saturated aqueous solution of NaHCO3 (100 mL) three times
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (eluting with 1:20 to 1:10 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-cb7352f72ed44d5494c9dc291be2083f
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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