Ethyl Acetate → (1-Naphthalen-1-yl-cyclopentyl)-acetonitrile

HRID 2169377Notes

Reaction equation

HRID 2169377 reaction equation
[C:1]1([C:11]2([CH2:16]OS(C)(=O)=O)[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C-:22]#[N:23].[Na+].C(OCC)(=O)C>CS(C)=O.CCCCCC>[C:1]1([C:11]2([CH2:16][C:22]#[N:23])[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 86726006Methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester

Product 1

HCID 86726007(1-Naphthalen-1-yl-cyclopentyl)-acetonitrileYield 44%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester (341) (2.1 g, 6.90 mmol) in dimethyl sulfoxide (10.0 mL) were added KI (115 mg, 0.69 mmol) and NaCN (507 mg, 10.35 mmol) and the reaction mixture was stirred at 140° C. for 2 h (silica TLC, 10% ethyl acetate in hexane; Rf=0.5). The reaction mass was cooled to room temperature, quenched with FeSO4 solution (15 mL) and diluted with water (100 mL). The resulting solid was separated through filtration and washed well with ethyl acetate. The biphasic layer was separated in a separating funnel. The organic part was washed with brine (2×50 mL), dried and concentrated in vacuo to get a crude mass which was purified by Combi-Flash using a mixture of ethyl acetate and hexane as gradient eluent to get pure (1-naphthalen-1-yl-cyclopentyl)-acetonitrile (342) (710 mg, 44%) as a yellow gummy liquid.

Workup

  1. customquenched with FeSO4 solution (15 mL)
  2. additiondiluted with water (100 mL)
  3. customThe resulting solid was separated through filtration
  4. washwashed well with ethyl acetate
  5. customThe biphasic layer was separated in a separating funnel
  6. washThe organic part was washed with brine (2×50 mL)
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto get a crude mass which
  10. customwas purified by Combi-Flash
  11. additiona mixture of ethyl acetate and hexane as gradient eluent

Sources & evidence

ORD record
ord-63fbbb5efd294733a06b95a2a2c166ae
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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