Potassium Hydroxide → methyl N-[(2-chloro-5-ethynylphenyl)methyl]carbamate

HRID 70247Notes

Reaction equation

HRID 70247 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si](C)(C)C)=[CH:4][C:3]=1[CH2:14][NH:15][C:16](=[O:19])[O:17][CH3:18].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][C:3]=1[CH2:14][NH:15][C:16](=[O:19])[O:17][CH3:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66789132methyl N-[[2-chloro-5-[2-(trimethylsilyl)ethynyl]phenyl]methyl]-carbamate2×

Product 1

HCID 86641518methyl N-[(2-chloro-5-ethynylphenyl)methyl]carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl N-[[2-chloro-5-[2-(trimethylsilyl)ethynyl]phenyl]methyl]-carbamate (i.e. the product of Step C) (1.37 g, 4.6 mmol) in methanol (28 mL) was added potassium hydroxide (2.3 mL, 1M in methanol). The reaction mixture was stirred at room temperature for 18 h, and then concentrated. The resulting residue was partitioned between ethyl acetate and water, the organic layer was separated, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a brown oil (0.90 g).

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was partitioned between ethyl acetate and water
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-335991bc799843a988fefc58f96d603a
Source dataset
uspto-grants-2014_09
Patent number
US08822521B2

Reaction notes

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