Tetrahydrofuran → 4-(Hydroxymethyl)-3-methylbenzonitrile

HRID 514500ノート

反応式

HRID 514500 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 183278964-(Hydroxymethyl)-3-methylbenzonitrile収率 62%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f860297523bd4097a2859a3bc3165f8a
出典データセット
uspto-grants-2015_08
特許番号
US09107916B2

反応ノート

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