HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 355204Generated: October 29, 2026
Imidazole → (3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate
https://huagongshe.com/reaction/355204
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | (3aR,4S,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one | HCID 2724454 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | (3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate | HCID 2724503 | — |
Reaction Steps
A solution of 16.58 g of (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one in 18 ml of dimethylformamide is combined at 0° C. with 10.21 g of imidazole and 10.85 g of tert.-butyldimethylsilyl chloride. The mixture is stirred for 24 hours at 20° C., diluted with 1.5 l of ether, shaken in succession with 5% sulfuric acid and brine, dried over magnesium sulfate, and evaporated under vacuum. The residue is recrystallized from hexane.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04378370 |
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| Source dataset | uspto-grants-1983_03 |
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| ORD ID | ord-f6afcd1fcd7a4609b4668316af90c450 |
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| Source note | uspto-grants-1983_03 |
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