Tetrahydrofuran → HCID 20028734, compound

HRID 1722357Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:20][CH:21]([OH:29])[CH2:22][S:23][CH2:24][CH:25]([OH:28])[CH2:26][OH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:30]1CCC[CH2:31]1>CCOCC>[CH2:1]([O:8][C:9]1[C:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:20][CH:21]([OH:29])[CH2:22][S:23][CH2:24][CH:25]1[CH2:26][O:27][C:31](=[O:30])[O:28]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

200 mg (0.48 mmol) of 7-(2-benzyloxy-3-cyclopentylphenyl)-4-thiaheptane-1,2,6-triol (Example 11) are dissolved in 3 ml of tetrahydrofuran, and 150 mg (0.93 mmol) of N,N'-carbonyldiimidazole are added. The solution is stirred at 70° C. with exclusion of moisture for 5 h and then diluted with ether and washed once with 1N sodium hydroxide solution and twice with saturated brine. Drying over sodium sulfate, removal of the solvent by distillation in vacuo and chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 1:1) yields 133 mg of 4-[5-(2-benzyloxy-3-cyclopentylphenyl)-4-hydroxy-2-thiapentyl]-1,3-dioxolan-2-one.

Workup

washwashed once with 1N sodium hydroxide solution and twice with saturated brine
dry with materialDrying over sodium sulfate, removal of the solvent by distillation in vacuo and chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-b8dbee6a1bd146a19d52e25b2aa1f760
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04855323

Reaction notes

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