Lithium borohydride → 2-(2-Chloro-4-cyano-5-methoxyphenyl)ethanol

HRID 1474253Notes

Reaction equation

HRID 1474253 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][C:13](OC)=[O:14].[BH4-].[Li+]>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][CH2:13][OH:14]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 77231255Methyl (2-chloro-4-cyano-5-methoxyphenyl)acetate

Product 1

HCID 666440092-(2-Chloro-4-cyano-5-methoxyphenyl)ethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2-chloro-4-cyano-5-methoxyphenyl)acetate (200 mg, 0.835 mmol) in THF (5 mL) was added 2M lithium borohydride (0.835 mL, 1.67 mmol) and the reaction was stirred at RT for 16 hours. The reaction was diluted with ether and quenched into water containing 2N HCl. The mixture was extracted twice with ethyl acetate and the organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The product mixture was separated by MPLC (40+S; 20-60% ethyl acetate/hexanes) to afford the title product. 1H-NMR (400 MHz, CDCl3) δ ppm 3.04 (t, J=6.4 Hz, 2H), 3.93 (t, J=6.4 Hz, 2H), 3.93 (s, 3H), 6.927 (s, 1H), 7.536 (s, 1H).

Workup

  1. customquenched into water containing 2N HCl
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washthe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product mixture was separated by MPLC (40+S; 20-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d18835227d0540f690623d6ad26e93c8
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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