Chloroiodomethane → HCID 86596139, compound

HRID 2222924Notes

Reaction equation

HRID 2222924 reaction equation
[Zn]([CH2:4][CH3:5])[CH2:2][CH3:3].Cl[CH2:7]I.[OH:9][CH2:10][CH:11]1[CH:16]([C:17]([O-:19])=[O:18])[CH:15]=[CH:14][CH2:13][CH2:12]1>ClCCCl>[C:17]1(=[O:18])[O:19][CH2:10][CH:11]2[CH2:12][CH2:13][CH:5]3[CH2:4][CH:15]3[CH:16]12.[OH:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH:14]2[CH:15]([CH2:7]2)[CH:16]1[C:17]([O:19][CH2:2][CH3:3])=[O:18]

Participants

6

Reactant 3

HCID 11644ChloroiodomethaneHCID 86596142HCID 86596142, compoundHCID 178418750HCID 178418750, compound

Product 2

HCID 86596139HCID 86596139, compoundHCID 91478051HCID 91478051, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 1,2-dichloroethane (100 mL) at 0° C. and under a dry nitrogen atmosphere was added Et2Zn (neat, 5.2 mL, 50.0 mmol) dropwise followed by chloroiodomethane (7.72 mL, 106.0 mmol) and the reaction mixture was stirred 5 min. (1R/S,6R/S)-6-(Hydroxymethyl)cyclohex-2-ene-1-carboxylate (3.67 g, 20.0 mmol) was then added and the reaction mixture was stirred 1 h at 0° C. followed by overnight stirring at room temperature. The reaction mixture was carefully quenched with water, the product extracted with ether, and dried on anhydrous sodium sulfate. The solvent was removed in vacuo and the product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 2/8) to afford the desired product (3αR/S,5αS/R,6αR/S,6βR/S)-octahydro-1H-cyclopropa[3,4]benzo[1,2-c]furan-1-one along with some of the uncyclized product ethyl(2R/S,3R/S)-3-(hydroxymethyl)bicyclo[4.1.0]heptane-2-carboxylate.

Workup

  1. additionwas then added
  2. waitfollowed by overnight
  3. stirringstirring at room temperature
  4. customThe reaction mixture was carefully quenched with water
  5. extractionthe product extracted with ether
  6. dry with materialdried on anhydrous sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 2/8)

Sources & evidence

ORD record
ord-4f787197f1324231ba802fad42bfc733
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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