Methyl iodide → HCID 10405126, compound

HRID 1376533Notes

Reaction equation

HRID 1376533 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][CH2:12][CH2:11][C:10]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:26]I>C1COCC1>[CH3:26][O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][CH2:12][CH2:11][C:10]=2[C:14]2[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 104266611-[2-(4-Hydroxymethylphenyl)cyclopenten-1-yl]-4-(methylsulfonyl)benzene

Product 1

HCID 10405126HCID 10405126, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, a stirred solution of 79 mg (0.24 mmol) of 1-[2-(4-hydroxymethylphenyl)cyclopenten-1-yl]-4-(methylsulfonyl)benzene (Example 9) in 2 mL of dry THF at 0° C. was treated with 15 mg (0.6 mmol) of sodium hydride (95%). After 30 minutes, 0.1 mL (1.6 mmol) of methyl iodide was added and the reaction was allowed to warm to ambient temperature overnight. The solvent was removed in vacuo; the residue was dissolved in ethyl acetate and washed with water, dried (MgSO4), and reconcentrated. Purification by silica gel chromatography (MPLC) with hexane/ethyl acetate (5:1) and subsequent lyophilization from acetonitrile/water (1:1) gave 25 mg (30%) of 1-[2-(4-methoxymethylphenyl)cyclopenten-1-yl]-4-(methylsulfonyl)benzene as a colorless solid: NMR (CDCl3) δ2.09 (m, J=7 Hz, 2H), 2.92 (t, J=7 Hz, 4H), 3.03 (s, 3H), 3.40 (s, 3H), 4.42 (s, 2H), 7.12 (d, J=8 Hz, 2H), 7.20 (d, J=8 Hz, 2H), 7.33 (d, J=8 Hz, 2H), 7.73 (d, J=8 Hz, 2H); MS (EI) m/e (rel intensity) 342 (100), 81 (27), 69 (62). HRMS. Calc'd for C20H22O3S: 342.1290. Found: 342.1301. Anal. Calc'd for C20H22O3S: C, 70.15; H, 6.48; S, 9.36. Found: C, 69.86; H, 6.64; S, 9.38.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customPurification by silica gel chromatography (MPLC) with hexane/ethyl acetate (5:1) and subsequent lyophilization from acetonitrile/water (1:1)

Sources & evidence

ORD record
ord-853d043ebcd345daa045f2d4591e7056
Source dataset
uspto-grants-1997_09
Patent number
US05663180

Reaction notes

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