Toluene → HCID 118510814, compound

HRID 1053799Notes

Reaction equation

[Si](O[C@@H:9]1[CH2:13][C:12](=[O:14])[C@H:11]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)[C@H:10]1/[CH:27]=[CH:28]/[CH:29]([O:41][Si](C(C)(C)C)(C)C)[CH2:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)(C(C)(C)C)(C)C.C1(C)C=CC=CC=1>CC(O)=O.O.C1COCC1>[OH:41][CH:29]([CH2:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)/[CH:28]=[CH:27]/[C@H:10]1[CH:9]=[CH:13][C:12](=[O:14])[C@@H:11]1[CH2:15][CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of methyl 4-(2-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((E)-3-((tert-butyldimethylsilyl)oxy)-4-(naphthalen-2-yl)but-1-en-1-yl)-5-oxocyclopentyl)ethyl)benzoate (1 g, 1.46 mmol) in HOAc/H2O/THF (32 mL, 2:1:1) was stirred at 70° C. overnight and then was co-evaporated with toluene. Purification of the residue by flash chromatography (ethyl acetate/hexanes) gave methyl 4-(2-((1R,2S)-2-((E)-3-hydroxy-4-(naphthalen-2-yl)but-1-en-1-yl)-5-oxocyclopent-3-en-1-yl)ethyl)benzoate (497 mg, 77%).

Workup

customPurification of the residue by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-a5bbabaa82ca4cc7894cda01d2b647cd
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394273B2

Reaction notes

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