Lithium borohydride → HCID 66643840, compound

HRID 1474249Notes

Reaction equation

HRID 1474249 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([C:10]#[N:11])[CH:5]=[CH:4][C:3]=1[CH2:12][C:13](OC)=[O:14].[BH4-].[Li+]>C1COCC1.CCOCC>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([C:10]#[N:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][OH:14]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 77231256HCID 77231256, compound

Product 1

HCID 66643840HCID 66643840, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2-chloro-4-cyano-3-methoxyphenyl)acetate (700 mg, 2.92 mmol) in THF (30 mL) was added 2M lithium borohydride (1.46 mL, 2.92 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 flash chromatography (10-40% ethyl acetate/hexanes) to afford the title product. 1H-NMR (400 MHz, CDCl3) δ ppm 3.10 (t, J=6.4 Hz, 2H), 3.94 (t, J=6.4 Hz, 2H), 4.08 (s, 3H), 7.175 (d, J=7.8 Hz, 1H), 7.46 (d, J=7.8 Hz, 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 flash chromatography (10-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a967a803ad824b88860dfaf1e5440374
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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