Diethyl Ether → (6-(Propan-2-yl)pyridin-2-yl)methanol

HRID 706534노트

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HRID 706534 반응식
[CH:1]([C:4]1[N:9]=[C:8]([C:10](OCC)=[O:11])[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC>C1COCC1>[CH:1]([C:4]1[N:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 67974663Ethyl 6-isopropylpicolinate

생성물 1

HCID 21874757(6-(Propan-2-yl)pyridin-2-yl)methanol수율 54.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Ethyl 6-isopropylpicolinate (prepared as in Preparation C; 75 g, 0.39 mol) was dissolved in 1.5 liters of dry THF, chilled to 0° C. and lithium aluminum hydride (0.39 L, 0.39 mol, 1M in THF) was added slowly over a 20 minute period. The resulting dark solution was stirred at 0° C. for 30 minutes, then allowed to warm to ambient temperature. TLC showed complete consumption of starting material. The reaction mixture was chilled to 0° C. and quenched carefully by the addition of sodium sulfate decahydrate until no gas evolution was observed. A thick mixture resulted. Celite and ether (about 200 mL) were added and the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to give 32 g of brown oil. The filter cake was slurried in IPA/EtOAc overnight and filtered to give an additional 8 g of product (68%).

후처리

  1. temperatureto warm to ambient temperature
  2. customconsumption of starting material
  3. temperatureThe reaction mixture was chilled to 0° C.
  4. customquenched carefully by the addition of sodium sulfate decahydrate until no gas evolution
  5. customA thick mixture resulted
  6. filtrationthe reaction mixture was filtered
  7. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e3d4198cf1494d29870de86001db7457
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

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