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Lithium borohydride → (1-Isopropyl-1H-indol-6-yl)methanol

HRID 1510130
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HRID 1510130 반응식
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13](OC)=[O:14])[CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2].[BH4-].[Li+]>C1COCC1>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][OH:14])[CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2]
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참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 10608809Methyl 1-isopropyl-1H-indole-6-carboxylate

생성물 1

HCID 29038143(1-Isopropyl-1H-indol-6-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a 0° C. solution of methyl 1-isopropyl-1H-indole-6-carboxylate (0.50 g, 2.30 mmol) in THF (5 mL) was added 1M lithium borohydride in THF (6.90 mL, 6.90 mmol). After stirring at rt for 96 h, quenched with MeOH and let stir for 1 h. The reaction mixture was concentrated, partitioned between saturated sodium bicarbonate and EtOAc, washed with H2O and brine, dried with Na2SO4, and concentrated. The crude compound was chromatographed to give the desired product.

후처리

  1. customquenched with MeOH
  2. stirringlet stir for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. custompartitioned between saturated sodium bicarbonate and EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customThe crude compound was chromatographed

출처 및 근거

ORD 기록
ord-8b2dc08af4b54059a33313d5c61c1fd7
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08211904B2

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