Methyl iodide → HCID 58968732, compound

HRID 2075097Notes

Reaction equation

HRID 2075097 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1[C:20]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:30]>O1CCCC1>[CH3:30][O:26][C:20]1([C:11]2[CH:12]=[CH:13][C:14]([C:16]([F:17])([F:18])[F:19])=[CH:15][C:10]=2[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 589687241-(2-((Tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)phenyl)cyclohexanol

Product 1

HCID 58968732HCID 58968732, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)phenyl)cyclohexanol (108 mg; 0.278 mmol) in tetrahydrofuran (2 mL) at 0° C. was added sodium hydride (22 mg; 0.55 mmol). The reaction was stirred at 0° C. for 30 minutes. Then iodomethane (50 uL; 0.80 mmol) was added. The reaction was stirred at 0° C. for 30 minutes and then at room temperature for 16 hours. More iodomethane (20 uL; 0.32 mmol) was added and stirred for 4 hours. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The crude was purified over a 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-15% ethyl acetate in heptane) to give 63 mg (55%) the title compound as a colorless oil. MS-GC (El): Calc: 402.5, Found: 383 (M−F). 1H NMR (400 MHz, CDCl3) δ ppm 7.51 (d, J=7.88 Hz, 1H), 7.46 (d, J=7.47 Hz, 1H), 7.35 (d, J=8.30 Hz, 1H), 5.05 (s, 2H), 2.94 (s, 3H), 2.16 (d, J=12.45 Hz, 2H), 1.8-1.56 (m, 8H), 0.98 (s, 9H), 0.13 (s, 6H).

Workup

  1. stirringThe reaction was stirred at 0° C. for 30 minutes
  2. waitat room temperature for 16 hours
  3. stirringstirred for 4 hours
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude was purified over a 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-15% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-cdd32dad70ea44f29e8d2765e231f718
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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