HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1683976Generated: October 26, 2026
Diisobutylaluminum hydride → 2-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) cyclopropyl]ethanol
https://huagongshe.com/reaction/1683976
Participants
| Role | Name | HCID | Charge |
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| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | Methyl [1-(1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetate | HCID 53800337 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) cyclopropyl]ethanol | HCID 54554275 | 77% |
Reaction Steps
To a -78° C. solution of ester from Step 7 (442 mg, 1 mmol) in 5 mL THF was added DIBAH (1.5M in toluene, 2 mL, 3 mmol), and the mixture was stirred for 2 hours with slow warming to 0° C. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was filtered through a plug of silica gel to give 319 mg of the title compound which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05639780 |
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| Source dataset | uspto-grants-1997_06 |
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| ORD ID | ord-269b11486e864ab3bc0d1163300f15f4 |
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| Source note | uspto-grants-1997_06 |
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