Diiodomethane → HCID 15542197, compound

HRID 1421082Notes

Reaction equation

HRID 1421082 reaction equation
[Zn](CC)[CH2:2]C.C(I)I.[CH3:9][C:10]1([CH3:31])[O:14][C:13](=[O:15])[C:12]([O:16][CH2:17][C:18]([CH3:20])=[CH2:19])=[C:11]1[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)CCl>[CH3:9][C:10]1([CH3:31])[O:14][C:13](=[O:15])[C:12]([O:16][CH2:17][C:18]2([CH3:2])[CH2:20][CH2:19]2)=[C:11]1[C:21]1[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 15542196HCID 15542196, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 15542197HCID 15542197, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of Et2Zn (0.82 mL) in 50 mL of ClCH2CH2Cl cooled at 0∞C. was added 1.3 mL of CH2I2 slowly. The mixture was stirred for 5 min. and treated with 0.63 g of the olefin of example 18 at 0∞C. The mixture was stirred for 20 min. at 0∞C. and 3 h at room temperature. The reaction was quenched by addition of 50 mL of saturated NH4Cl solution and the product was extracted with EtOAc (200 mL) The extract was dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromotography eluted with 3:2 hexane/EtOAc to give 400 mg of the title product as a white solid.

Workup

  1. stirringThe mixture was stirred for 20 min. at 0∞C
  2. custom3 h
  3. customat room temperature
  4. customThe reaction was quenched by addition of 50 mL of saturated NH4Cl solution
  5. extractionthe product was extracted with EtOAc (200 mL) The extract
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromotography
  10. washeluted with 3:2 hexane/EtOAc

Sources & evidence

ORD record
ord-5c340f5c1e694c73b1cb0bfd74536098
Source dataset
uspto-grants-2000_06
Patent number
US06071954

Reaction notes

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