Diiodomethane → HCID 59779153, compound

HRID 1096720Notes

Reaction equation

HRID 1096720 reaction equation
[Zn](CC)[CH2:2]C.C(I)I.[Cl:9][C:10]1[CH:11]=[C:12]([C:17]2[CH2:21][CH2:20][CH:19]([OH:22])[CH:18]=2)[CH:13]=[CH:14][C:15]=1[Cl:16]>C(Cl)Cl>[Cl:9][C:10]1[CH:11]=[C:12]([C:17]23[CH2:2][CH:18]2[CH:19]([OH:22])[CH2:20][CH2:21]3)[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 59779123HCID 59779123, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 59779153HCID 59779153, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an Et2Zn solution (1.0M in hexane; 14 mL, 14 mmol) cooled to 0° C., a solution of CH2I2 (1.13 mL, 14 mmol) in CH2Cl2 (10 mL) was added. This was stirred for 5 min, then a solution of 3-(3,4-dichlorophenyl)cyclopent-2-en-1-ol (0.5 g, 2.19 mmol) in CH2Cl2 (50 mL) was added dropwise. The reaction mixture was stirred overnight then quenched with saturated aqueous NH4Cl. The reaction mixture was extracted with CH2Cl2 (3×). The combined organic phases were dried over MgSO4 and concentrated in vacuo. Purification of the crude material by silica gel chromatography using 10-30% EtOAc/Heptane as the eluting solvent gave the target compound (0.3 g, 64%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.76-0.85 (m, 1 H) 1.20-1.33 (m, 2 H) 1.65-1.77 (broad, 1 H) 1.83-1.90 (m, 1 H) 1.93-2.17 (m, 3 H) 4.64-4.73 (m, 1 H) 6.93-6.97 (m, 1 H) 7.22 (d, 1 H) 7.29-7.34 (m, 1 H).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customthen quenched with saturated aqueous NH4Cl
  3. extractionThe reaction mixture was extracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude material by silica gel chromatography

Sources & evidence

ORD record
ord-b1cae54648ac4e87a429fa961f952953
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

Loading…