Diiodomethane → HCID 86723561, compound

HRID 2201655Notes

Reaction equation

HRID 2201655 reaction equation
[CH2:1]([Zn]CC)C.C(=O)=O.CC(C)=O.ICI.[CH2:16]=[C:17]1[CH2:20][CH:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:18]1>ClCCl.O>[CH2:1]1[C:17]2([CH2:18][CH:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[CH2:20]2)[CH2:16]1

Participants

7

Reactant 4

HCID 6346DiiodomethaneHCID 18522661Acetone cardiceHCID 28875369tert-butyl N-(3-methylidenecyclobutyl)carbamateHCID 178418750HCID 178418750, compound

Product 1

HCID 86723561HCID 86723561, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Diethyl zinc (40 mL, 1N hexane solution) was added to 100 mL of anhydrous dichloromethane under nitrogen. After the addition, cooled to −78° C. with dry ice-acetone, and diiodomethane (15 g, 56 mmol) was slowly added dropwise. After the addition stirring was continued for 30 minutes, and then changed into the ice-water bath. A solution of Compound 3-2 (1.7 g, 9.3 mmol) dissolved in 100 mL of dichloromethane was further added dropwise and stirred overnight, added 200 mL of water to quench the reaction, liquid separated, and the aqueous phase was extracted with 200 mL of dichloromethane three times. The organic phases were combined, rotary evaporated to remove solvents, and purified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1) to give

Workup

  1. additionAfter the addition
  2. additionwas slowly added dropwise
  3. additionAfter the addition
  4. additionwas further added dropwise
  5. stirringstirred overnight
  6. customto quench
  7. customthe reaction, liquid
  8. customseparated
  9. extractionthe aqueous phase was extracted with 200 mL of dichloromethane three times
  10. customrotary evaporated
  11. customto remove solvents
  12. custompurified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1)
  13. customto give

Sources & evidence

ORD record
ord-6c19b8e7ef534b92bfe3d8280f99fe1e
Source dataset
uspto-grants-2016_06
Patent number
US09365499B2

Reaction notes

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