Methyl iodide → HCID 123535377, compound

HRID 1471363Notes

Reaction equation

HRID 1471363 reaction equation
[S:1]1[C:5]([CH2:6][C:7]2[C:8]([CH3:25])=[C:9]([CH3:24])[C:10]([OH:23])=[C:11]([CH:13]3[CH:18]([OH:19])[CH:17]([OH:20])[CH2:16][CH:15]([CH2:21][OH:22])[O:14]3)[CH:12]=2)=[CH:4][C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]1=2.[C:30]([O-])([O-])=O.[Cs+].[Cs+].CI>CC(C)=O>[S:1]1[C:5]([CH2:6][C:7]2[C:8]([CH3:25])=[C:9]([CH3:24])[C:10]([O:23][CH3:30])=[C:11]([CH:13]3[CH:18]([OH:19])[CH:17]([OH:20])[CH2:16][CH:15]([CH2:21][OH:22])[O:14]3)[CH:12]=2)=[CH:4][C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 123711362HCID 123711362, compound

Product 1

HCID 123535377HCID 123535377, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 20 ml vial was charged with 22 (38.2 mg, 0.09 mmol) and Cs2CO3 (45 mg, 0.14 mmol) and to which was added 1 ml of dry acetone, followed by methyl iodide (12 μL, 0.18 mmol). The resulting mixture was stirred at room temperature for 16 h and the solid was filtered of, washed with acetone. The solvent was evaporated and the crude residue was purified by flash column chromatography on silica gel (4 g column, EtOAc/heptane: 0>>>100%) to afford 28.4 mg (71.8%) of 23 as a white solid. 1H NMR (CD3OD) δ 7.71 (d, J=7.58 Hz, 1H), 7.60 (d, J=7.58 Hz, 1H), 7.14-7.28 (3H), 6.87 (s, 1H), 4.52 (d, J=9.60 Hz, 1H), 4.22 (s, 2H), 3.76 (s, 3H), 3.65-3.75 (m, 2H), 3.49-3.59 (m, 3H), 2.23 (s, 3H), 2.20 (s, 3H), 2.02 (m, 1H), 1.50 (q, J=11.62 Hz, 1H). MS (ES) 451.1 (M+Na+).

Workup

  1. filtrationthe solid was filtered of,
  2. washwashed with acetone
  3. customThe solvent was evaporated
  4. customthe crude residue was purified by flash column chromatography on silica gel (4 g column, EtOAc/heptane: 0>>>100%)

Sources & evidence

ORD record
ord-a86ff79bb8e0496d88f4955a94b9b257
Source dataset
uspto-grants-2015_04
Patent number
US09012412B2

Reaction notes

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