Dichloromethane → (1-Cyano-3-methylenecyclobutyl)methyl methanesulfonate

HRID 1692927Notes

Reaction equation

HRID 1692927 reaction equation
[OH:1][CH2:2][C:3]1([C:8]#[N:9])[CH2:6][C:5](=[CH2:7])[CH2:4]1.C(Cl)Cl.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>>[CH3:20][S:21]([O:1][CH2:2][C:3]1([C:8]#[N:9])[CH2:6][C:5](=[CH2:7])[CH2:4]1)(=[O:23])=[O:22]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 668243411-(Hydroxymethyl)-3-methylenecyclobutanecarbonitrile

Product 1

HCID 86634345(1-Cyano-3-methylenecyclobutyl)methyl methanesulfonate

Procedure

To a mixture of 1-(hydroxymethyl)-3-methylenecyclobutanecarbonitrile (0.756 g, 0.00614 mol) in methylene chloride (20 mL, 0.3 mol) was added triethylamine (1.28 mL, 0.00921 mol) followed by methanesulfonyl chloride (0.594 mL, 0.00767 mol) at 0° C. The reaction was stirred at rt for 1 h, quenched with water, and extracted with dichloromethane. The combined organic layers were washed with water, brine, and then dried over magnesium sulfate and evaporated to dryness. The residue was used directly in next step.

Workup

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-0376b633c68f467aa857b38fd6396419
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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