Diiodomethane → HCID 66637193, compound

HRID 1094662Notes

Reaction equation

HRID 1094662 reaction equation
[CH2:1]([Zn]CC)C.[CH2:6]=[C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:13]=[CH:12]2)[CH3:8].ClC(Cl)C.ICI>[Cl-].[NH4+]>[CH3:6][C:7]1([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:13]=[CH:12]3)[CH2:1][CH2:8]1

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 63651,1-DichloroethaneHCID 66636992HCID 66636992, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 66637193HCID 66637193, compoundYield 151.5%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

Diethylzinc (1.0 M in Hexane)(6.30 ml, 6.30 mmol) was added to a solution of methyl 6-(prop-1-en-2-yl)-2-naphthoate (0.57 g, 2.5 mmol).in dichloroethane at 0° C. Diiodomethane (1.01 ml, 12.6 mmol) was then added dropwise to the mixture solution and the resultant mixture was stirred at 60° C. for 20 h. The reaction mixture was cooled to room temperature, diluted with saturated aqueous ammonium chloride (30 mL), and the mixture was extracted with CH2Cl2 (30 ml×3). The combined organic layer was washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml), and the organic layer was dried over Na2SO4. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting with ethyl acetate-hexane (1:20) to give 0.91 g of the title compound as white solid. 1H NMR (270 MHz, CDCl3) ppm 0.75-0.95 (2H, m), 0.95-1.13 (2H, m), 1.52 (3H, s), 3.97 (3H, s), 7.41 (1H, d, J=9.9 Hz), 7.74 (1H, s), 7.82 (1H, d, J=7.8 Hz), 7.86 (1H, d, J=8.6 Hz), 8.04 (1H, d, J=8.6 Hz), 8.56 (1H, s). MS (ESI) m/z: not observed M+ peak.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (30 ml×3)
  2. washThe combined organic layer was washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
  3. dry with materialthe organic layer was dried over Na2SO4
  4. customRemoval of the solvent
  5. customgave a residue, which
  6. customwas chromatographed on a column of silica gel eluting with ethyl acetate-hexane (1:20)

Sources & evidence

ORD record
ord-3cc5b03b75d34ff5aeebedb05532baca
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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