Ethyl chloroformate → HCID 131724339, compound

HRID 2120485Notes

Reaction equation

HRID 2120485 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](/[C:11](/[CH3:15])=[CH:12]/[C:13]#[CH:14])[CH:6]=1.C([Li])CCC.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23].[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7](/[C:11](/[CH3:15])=[CH:12]/[C:13]#[C:14][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 87950526HCID 87950526, compoundHCID 178418339Butyllithium

Product 1

HCID 131724339HCID 131724339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

764 mg (3.78 mmol) of 1-methoxymethoxy-3-((E)-1-methylbut-1-en-3-ynyl)benzene are dissolved in 20 ml of anhydrous THF and the solution is cooled to −78° C. 1.8 ml (4.5 mmol) of a 2.5M butyllithium solution are then added dropwise and the reaction medium is stirred for 30 minutes at this temperature. 0.43 ml (4.5 mmol) of ethyl chloroformate are then added dropwise and then the reaction medium is brought to room temperature and stirred for 2 hours. After treating with a saturated ammonium chloride solution and extracting with ethyl acetate, the organic phase is dried and then concentrated under reduced pressure. After purification by chromatography on a silica column (ethyl acetate 10-heptane 90), a yellow oil is obtained (m=836 mg; Y=81%).

Workup

  1. customis brought to room temperature
  2. stirringstirred for 2 hours
  3. extractionextracting with ethyl acetate
  4. customthe organic phase is dried
  5. concentrationconcentrated under reduced pressure
  6. customAfter purification by chromatography on a silica column (ethyl acetate 10-heptane 90)
  7. customa yellow oil is obtained (m=836 mg; Y=81%)

Sources & evidence

ORD record
ord-b41be1998f674e4897d3c2fd51317352
Source dataset
uspto-grants-2004_02
Patent number
US06689922B1

Reaction notes

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