Acetic Acid → HCID 121396293, compound

HRID 60701Notes

Reaction equation

[CH3:1][C:2]1(C)[O:6][C@H:5]2[O:7][C@H:8]([C@@H:10]([O:13][C:14](=[O:16])[CH3:15])[CH2:11][CH3:12])[CH2:9][C@H:4]2[O:3]1.[C:18]([OH:21])(=[O:20])[CH3:19].C(OC(=O)C)(=O)C.OS(O)(=O)=O>C(Cl)Cl>[C:18]([O:21][C@@H:4]1[CH2:9][C@@H:8]([C@@H:10]([O:13][C:14](=[O:16])[CH3:15])[CH2:11][CH3:12])[O:7][CH:5]1[O:6][C:2](=[O:3])[CH3:1])(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 22 °C

Procedure

To a solution of [(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propyl]acetate (compound 6f, 4.8 g, 20 mmol), acetic acid (12.2 g, 200 mmol) and acetic anhydride (10.2 g, 100 mmol) in anhydrous DCM (100 mL) was added concentrated H2SO4 (0.5 mL) at 0° C. After being stirred at 22° C. for 3 hours, the reaction was quenched by addition of saturated NaHCO3 solution. The organic layer was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column on silica gel (eluting with 1:8 EtOAc in petroleum ether) to afford 2.3 g of [(3R,5S)-2-acetoxy-5-[(1S)-1-acetoxypropyl]tetrahydrofuran-3-yl] acetate (compound 6g) as a colourless oil.

Workup

customthe reaction was quenched by addition of saturated NaHCO3 solution
customThe organic layer was separated
extractionthe aqueous phase was extracted with EtOAc
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column on silica gel (eluting with 1:8 EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-de8076c3f37a402c807aef266fc4207d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09441008B2

Reaction notes

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