Methyl iodide → HCID 118222076, compound

HRID 520215Notes

Reaction equation

HRID 520215 reaction equation
[OH:1][C@@:2]1(/[CH:12]=[CH:13]/[C:14](/[CH3:20])=[CH:15]\[C:16]([O:18][CH3:19])=[O:17])[C:7]([CH3:9])([CH3:8])[CH2:6][C:5](=[O:10])[CH:4]=[C:3]1[CH3:11].[CH3:21][Si](C)(C)N[Si](C)(C)C.[Li].CI>O1CCCC1>[OH:1][C@@:2]1(/[CH:12]=[CH:13]/[C:14](/[CH3:20])=[CH:15]\[C:16]([O:18][CH3:19])=[O:17])[C:7]([CH3:9])([CH3:8])[CH2:6][C:5](=[O:10])[C:4]([CH3:21])=[C:3]1[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10084943HCID 10084943, compoundHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 118222076HCID 118222076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of Example 1a (27.8 g, 0.1 mole) in anhydrous tetrahydrofuran (THF, 600 ml) was cooled to 0° C. with an ice bath under an atmosphere of nitrogen. Lithium hexamethyl disilazane (1.0 M solution in THF, 150 ml) was added dropwise via a syringe over about 30 minutes. The resulting solution was stirred at 0° C. for 30 minutes and the ice bath was removed. A solution of methyl iodide (8.09 ml, 18.4 g, 0.13 mole) in anhydrous THF (20 ml) was added via a syringe over 20 minutes. The resulting solution was stirred at ambient temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride solution (200 ml) and water (200 ml) and extracted with ethyl acetate (3×150 ml). The combined organic solution was dried (MgSO4), filtered and concentrated. The residue was purified on a silica gel column eluted with ethyl acetate and hexane. The title compound was obtained as a white solid (17.1 g). 1HNMR (CDCl3): δ7.84 (d, 1H), 6.16 (d, 1H), 5.75 (s, 1H), 3.70 (s, 3H), 2.44 (d, 1H), 2.34 (d, 1H), 2.00 (s, 3H), 1.88 (s, 3H), 1.83 (s, 3H), 1.07 (s, 3H), 1.00 (s, 3H). MS (ESI—): m/e=291.

Workup

  1. customthe ice bath was removed
  2. stirringThe resulting solution was stirred at ambient temperature overnight
  3. customThe reaction was quenched with saturated aqueous ammonium chloride solution (200 ml) and water (200 ml)
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. dry with materialThe combined organic solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on a silica gel column
  9. washeluted with ethyl acetate and hexane

Sources & evidence

ORD record
ord-b2cb491c33dc4ea98c04cf81bc925ef6
Source dataset
uspto-grants-2016_05
Patent number
US09326508B2

Reaction notes

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