Acetic Anhydride → HCID 121396355, compound

HRID 60700Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[O:7][C@H:8]([C@@H:10]([OH:13])[CH2:11][CH3:12])[CH2:9][C@H:4]2[O:3]1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:14][C:2]1([CH3:1])[O:6][C@H:5]2[O:7][C@H:8]([C@@H:10]([O:13][C:15](=[O:17])[CH3:16])[CH2:11][CH3:12])[CH2:9][C@H:4]2[O:3]1

Participants

Conditions

Temperature: 22 °C

Procedure

To a stirred solution of (1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propan-1-ol (compound 6e, 13.5 g, 67 mmol), TEA (81 g, 804 mmol), DMAP (1.6 g, 13 mmol) in anhydrous DCM (150 mL) was added acetic anhydride (62 g, 603 mmol). After being stirred at 22° C. for 10 hours, the reaction was quenched by the saturated NaHCO3 solution. The organic layer was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:8 EtOAc in petroleum ether) to afford 13 g 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) as a colourless oil.

Workup

customthe reaction was quenched by the 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
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (eluting with 1:8 EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-1242d4b20c23453f9f7143e0afb81762
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09441008B2

Reaction notes

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