Water → 4-(2-Hydroxyethyl)-2-methoxybenzonitrile

HRID 1474229Notes

Reaction equation

HRID 1474229 reaction equation
[Li+].[BH4-].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](OCC)=[O:13])=[CH:7][C:6]=1[O:17][CH3:18])#[N:4].O>C1COCC1>[OH:13][CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]#[N:4])=[C:6]([O:17][CH3:18])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 66643843Ethyl 2-(4-cyano-3-methoxyphenyl)acetate

Product 1

HCID 542351984-(2-Hydroxyethyl)-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (1.7 mL, 3.4 mmol, 2 M in THF) was added to a stirred solution of ethyl (4-cyano-3-methoxyphenyl)acetate (0.50 g, 2.4 mmol) in THF (25 mL) at 0° C. The resulting solution was stirred for 12 h. Water (15 ml) was added, and the resulting solution was extracted with dichloromethane (2×50 ml). The combined organic layers were dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography eluting with EtOAc-Hexanes (7:3→1:1) to give 4-(2-hydroxyethyl)-2-methoxybenzonitrile. 1H NMR (500 MHz, CDCl3) δ 7.52 (d, 1H, J=7.0 Hz), 6.91 (d, 1H, J=7.8 Hz), 6.88 (s, 1H), 3.95 (s, 3H), 3.92 (t, 2H, J=6.4 Hz), 2.93 (t, 2H, J=6.4 Hz); LCMS: [(M+1)]+=178.3; tR=2.1 min.

Workup

  1. extractionthe resulting solution was extracted with dichloromethane (2×50 ml)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with EtOAc-Hexanes (7:3→1:1)

Sources & evidence

ORD record
ord-400c6b4645904aff9ce82bd687750621
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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