Water → 2-(6-Hydroxyhexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

HRID 1053938Notes

Reaction equation

CC1C=CC(S(O[CH:12]2[CH2:16][O:15][CH:14]3[CH:17]([OH:20])[CH2:18][O:19][CH:13]23)(=O)=O)=CC=1.[O:21]=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:31])[N:23]1[K].O>CS(C)=O>[OH:20][CH:17]1[CH:14]2[O:15][CH2:16][CH:12]([N:23]3[C:24](=[O:31])[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:22]3=[O:21])[CH:13]2[O:19][CH2:18]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (10.24 g, 34.1 mmol) in DMSO (60 mL) was added (1,3-dioxoisoindolin-2-yl)potassium (8.21 g, 44.3 mmol). The mixture was stirred under N2 atmosphere at 130° C. overnight then cooled down to room temperature, and poured into water. The resulting mixture was extracted with CH2C12 (300 mL×3), and the combined organic layers were washed with water (100 mL×3), dried over Na2SO4, and then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/1) to afford the title compound as a white solid (2.35 g, 25.0%).

Workup

temperaturethen cooled down to room temperature
extractionThe resulting mixture was extracted with CH2C12 (300 mL×3)
washthe combined organic layers were washed with water (100 mL×3)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/1)

Sources & evidence

ORD record: ord-cee9caea0efa4bc9915fbe0340ee87d8
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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