Tetrahydrofuran → 4-(Hydroxymethyl)-3-methylbenzonitrile

HRID 514500노트

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HRID 514500 반응식
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[C:5]([CH3:13])[CH:4]=1)#[N:2].C1COCC1.[Cl-].[Cl-].[Ca+2].[BH4-].[Na+]>O.C(O)C>[OH:8][CH2:7][C:6]1[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[CH3:13]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 18766060Methyl 4-cyano-2-methylbenzoate

생성물 1

HCID 183278964-(Hydroxymethyl)-3-methylbenzonitrile수율 62%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

Charge methyl 4-cyano-2-methylbenzoate (627 mg, 3.57 mmol), THF (12 mL) and ethanol (12 mL) to a flask, followed by CaCl2 (418 mg, 3.57 mmol) and NaBH4 (265 mg, 7.16 mmol). The mixture was then stirred at room temperature overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic extract was concentrated and purified by flash column chromatograph to give 325 mg of the title compound (62%). 1H NMR (300 MHz, CDCl3): δ 1.83 (1H, t, J=5.4 Hz), 2.33 (3H, s), 4.75 (2H, d, J=5.4 Hz), 7.43 (1H, s), 7.52-7.56 (2H, m).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. extractionThe organic extract
  3. concentrationwas concentrated
  4. custompurified by flash column chromatograph

출처 및 근거

ORD 기록
ord-f860297523bd4097a2859a3bc3165f8a
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107916B2

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