4-Toluenesulfonyl chloride → (1-Cyanocyclopropyl)methyl 4-methylbenzenesulfonate

HRID 708870Notes

Reaction equation

HRID 708870 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH:12][CH2:13][C:14]1([C:17]#[N:18])[CH2:16][CH2:15]1.CCN(CC)CC>ClCCl>[CH3:8][C:7]1[CH:9]=[CH:10][C:4]([S:1]([O:12][CH2:13][C:14]2([C:17]#[N:18])[CH2:16][CH2:15]2)(=[O:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 220282071-(Hydroxymethyl)cyclopropane-1-carbonitrile

Product 1

HCID 22028201(1-Cyanocyclopropyl)methyl 4-methylbenzenesulfonateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TsCl (7.25 g, 38 mmol) was added in one portion to a stirred solution of 1-(hydroxymethyl)cyclopropanecarbonitrile (3.1 h, 32 mmol) in dichloromethane (75 mL) at 0° C. Et3N (4.1 g, 40 mmol) was added. The reaction mixture was stirred at rt over night. The mixture was diluted with dichloromethane, washed with water, 0.5 N NaOH, brine. The organic extract was dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to give 18A (6.43 g, 81% yield) as a white solid.

Workup

  1. washwashed with water, 0.5 N NaOH, brine
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-b30724aab117442eb4d31beb67e8b4cd
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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