Tetrahydrofuran → 4-(Hydroxymethyl)-3-methylbenzonitrile

HRID 878656Notes

Reaction equation

HRID 878656 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-bc744282b12f4c899d6b7e63617ca65b
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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