Chloroiodomethane → HCID 66789942, compound

HRID 1510143Notes

Reaction equation

HRID 1510143 reaction equation
ClCI.[CH2:4]=[C:5]1[CH2:9][C@@H:8]([C:10]([O:12][CH3:13])=[O:11])[C@H:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1.[Zn](CC)[CH2:21]C>ClCCCl>[C:14]1([C@@H:7]2[CH2:6][C:5]3([CH2:21][CH2:4]3)[CH2:9][C@H:8]2[C:10]([O:12][CH3:13])=[O:11])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11644ChloroiodomethaneHCID 12537224Methyl 4-methylene-2-phenylcyclopentanecarboxylate, trans-HCID 178418750HCID 178418750, compound

Product 1

HCID 66789942HCID 66789942, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Chloroiodomethane (6.3 g, 35.5 mmol) was added to a 0° C. mixture containing 2.4 g (11.1 mmol) of methyl trans-4-methylene-2-phenylcyclopentanecarboxylate (J. Am. Chem. Soc. 1983, 105, 2315) in 25 mL of DCE followed by the addition of 17.8 mL (17.8 mmol) of Et2Zn (1M in hexanes). The reaction was stirred at 0° C. for 1 h before it was quenched with 1N HCl. The mixture was extracted with DCM (three times) and the combined extracts were dried over MgSO4 and concentrated. Column chromatography (9:1 Hexanes/EtOAc) afforded the desired compound as a colorless liquid.

Workup

  1. customwas quenched with 1N HCl
  2. extractionThe mixture was extracted with DCM (three times)
  3. dry with materialthe combined extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-89f9e0ed99664fa8b2cdf50b24b217c9
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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