Reaction #1583835

Reaction equation

methyl N-[[2-chloro-5-[2-(trimethylsilyl)ethynyl]phenyl]methyl]-carbamate

product

methyl N-[[2-chloro-5-[2-(trimethylsilyl)ethynyl]-phenyl]methyl]carbamate

potassium hydroxide

→

title compound

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

Solvents

methanol

Conditions

Workup

1. 1
   Concentrationconcentrated
2. 2
   OtherThe resulting residue was partitioned between ethyl acetate and water
3. 3
   Otherthe organic layer was separated
4. 4
   Washwashed with water
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under reduced pressure

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).

Source