Ethyl acetate hexane → HCID 136241951, compound

HRID 1844392Notes

Reaction equation

[C:1]1([C:7]#[C:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3CC(C)(C)C([O-])=O)[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CC[O:34]C(C)=O.CCCCCC>C1COCC1>[C:1]1([C:7]#[C:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([OH:34])=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(Phenylethynyl)quinoline-5-ylpivalate (15.4 mg, 0.0468 mmol) was dissolved in THF (0.78 mL), followed by cooling down to 0° C. After LiAlH4 (0.06 mL, 0.117 mmol) was added thereto, the resulting mixture was warmed to room temperature and stirred for 1 hr. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:1). When the reaction was completed, a saturated aqueous solution was added thereto, and the resulting mixture was extracted with diethylether, to thereby obtain an organic layer. The organic layer was dried over anhydrous MgSO4 and filtrated. The filtrate was concentrated under reduced pressure and purified by column chromatography (EtOAc/Hexane=1:1, R.f: 0.7), to thereby obtain 2-(phenylethynyl)quinoline-5-ol (5.6 mg, 49%) as a yellow solid.

Workup

temperaturethe resulting mixture was warmed to room temperature
additiona saturated aqueous solution was added
extractionthe resulting mixture was extracted with diethylether
customto thereby obtain an organic layer
dry with materialThe organic layer was dried over anhydrous MgSO4
filtrationfiltrated
concentrationThe filtrate was concentrated under reduced pressure
custompurified by column chromatography (EtOAc/Hexane=1:1, R.f: 0.7)

Sources & evidence

ORD record: ord-07bb8e9631e04f5a9e3ef28c8aacfda7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946431B2

Reaction notes

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