Sulfuric Acid → HCID 121396348, compound

HRID 60748Notes

Reaction equation

[C:1]([O:9][CH:10]([C@H:13]1[O:22][C@@H:16]2[O:17][C:18](C)(C)[O:19][C@@H:15]2[CH2:14]1)CC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.C([O-])(O)=O.[Na+]>CO>[C:1]([O:9][CH2:10][C@@H:13]1[CH2:14][C@H:15]([OH:19])[CH:16]([O:17][CH3:18])[O:22]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of [(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate (compound 32a, 5.1 g, 18 mmol) in MeOH (50 mL) was added H2SO4 (0.5 mL) at room temperature. After being stirred at 80° C. for 0.5 hour, the reaction mixture was cooled to room temperature, neutralized by solid NaHCO3 and concentrated in vacuo. The residue was re-dissolved in EtOAc, washed with water twice. The separated organic layer was dried over Na2SO4 and concentrated in vacuo to afford 4.1 g crude product of [(2S,4S)-4-hydroxy-5-methoxy-tetrahydrofuran-2-yl]methyl benzoate (compound 32b) as oil, which was used in next step directly. MS obsd. (ESI+) [(M+NH4)+]: 270.

Workup

temperaturethe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
dissolutionThe residue was re-dissolved in EtOAc
washwashed with water twice
dry with materialThe separated organic layer was dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-95684f106d344edab2f142487f316a72
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09441008B2

Reaction notes

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