Hydrogen Peroxide → HCID 70281683, compound

HRID 263679Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:12]/[CH:13]=[CH:14]/[C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH-].[Na+].OO>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:12]/[CH:13]=[CH:14]/[C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[C@@H:9]([OH:11])[CH3:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

1.95 of the ketone thus obtained was dissolved in 62 ml of tetrahydrofuran, and 7.0 ml of a 1M tetrahydrofuran solution of lithium tri-sec-butyl borohydride was added under cooling to -78° C. with stirring, followed by stirring at the same temperature for 30 minutes. To the reaction solution, 20 ml of a 0.5N sodium hydroxide aqueous solution was added, and then 10 ml of a 30% hydrogen peroxide aqueous solution was dropwise added thereto. After the dropwise addition, the mixture was stirred at room temperature for 30 minutes. The reaction solution was extracted by an addition of water and ethyl acetate, followed by conventional post-treatment. Then, purification was conducted by medium pressure liquid chromatography (hexane/ethyl acetate=5/1) to obtain 1.91 g of (2S*,3S*,5E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-ol.

Workup

stirringby stirring at the same temperature for 30 minutes
additionAfter the dropwise addition
stirringthe mixture was stirred at room temperature for 30 minutes
extractionThe reaction solution was extracted by an addition of water and ethyl acetate
customThen, purification

Sources & evidence

ORD record: ord-2b50b63d87d14a1a8e4713ff04cd9df1
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05643958

Reaction notes

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