1,10-Phenanthroline → 2-Methoxybenzyl alcohol

HRID 1883407Notes

Reaction equation

HRID 1883407 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:15]([O-])([O-])=[O:16].[Cs+].[Cs+].I[C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][OH:25]>[Cu]I.CO>[CH3:15][O:16][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][OH:25]

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 1076292-Iodobenzylic alcohol

Product 1

HCID 691542-Methoxybenzyl alcoholYield 88.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A test tube was charged with CuI (20 mg, 0.10 mmol, 10 mol %), 1,10-phenanthroline (36 mg, 0.20 mmol, 20 mol %), Cs2CO3 (456 mg, 1.4 mmol), 2-iodobenzylalcohol (234 mg, 1.0 mmol) and methanol (1.0 mL). The test tube was sealed and the reaction mixture was stirred at 80° C. for 24 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2×20 cm; pentane/diethyl ether 2:1) provided 122 mg (88% yield) of the title compound as a colorless oil.

Workup

  1. customThe test tube was sealed
  2. temperatureThe resulting suspension was cooled to room temperature
  3. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with diethyl ether
  4. concentrationThe filtrate was concentrated
  5. customPurification of the residue by flash chromatography on silica gel (2×20 cm; pentane/diethyl ether 2:1)

Sources & evidence

ORD record
ord-ba9b95b37f8a44cf896751c9821b5372
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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