Methyl chloroformate → HCID 86671793, compound

HRID 2172714Notes

Reaction equation

HRID 2172714 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([CH3:15])([CH3:14])[C:11](O)=[O:12])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.ClC(OC)=O.[N-:28]=[N+:29]=[N-:30].[Na+]>CC(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([CH3:15])([CH3:14])[C:11]([N:28]=[N+:29]=[N-:30])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 33557Sodium AzideHCID 62738841HCID 62738841, compound

Product 1

HCID 86671793HCID 86671793, compoundYield 26.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(3-methoxyphenyl)-2,2-dimethylpropanoic acid (200 mg, 0.96 mmol) in acetone (40 mL) and water (4 mL) was cooled to 0° C. Triethyl amine (0.18 mL, 1.3 mmol) was added to the reaction mixture followed by methyl chloroformate (118 mg, 1.25 mmol). The mixture was stirred for 1 hour at 0° C. and then another solution of sodium azide (94 mg, 1.45 mmol) in water (1 mL) was added dropwise. The reaction mixture was stirred at room temperature for another 1 hour. The mixture was diluted with water and extracted with ethyl acetate. The combined organic fractions were washed with water, dried over sodium sulfate and concentrated to give 3-(3-methoxyphenyl)-2,2-dimethylpropanoyl azide (60 mg) as a crude yellow oil, which was used without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for another 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe combined organic fractions were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-75236f3f042048c38a648c481a00aba3
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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