Oxygen → 1-Phenyl-3-heptanol

HRID 650326Notes

Reaction equation

HRID 650326 reaction equation
[BH3-]C#N.[Na+].C([OH:9])(C)(C)C.I[CH:11]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O=O>O>[C:14]1([CH2:13][CH2:12][CH:11]([OH:9])[CH2:20][CH2:21][CH2:22][CH3:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 977OxygenHCID 6386tert-ButanolHCID 5003444Sodium cyanoborohydrideHCID 109027103-Iodo-1-phenylheptane

Product 1

HCID 104201101-Phenyl-3-heptanolYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel (30 ml, a two-neck, eggplant type flask) is subjected to nitrogen gas purging and NaBH3CN (0.5 mmol, 31.4 mg), Bu2(t-Bu)SnCl (0.0125 mmol, 4.1 mg, 3.5 μl) and tert-butanol (1 ml) are added. Then, 3-iodo-1-phenylheptane (0.25 mmol, 75.5 mg, 57.5 g 1) is added to the solution. The introduction of nitrogen gas is discontinued, a nitrogen gas-filled black butyl rubber balloon is set instead, and oxygen (0.375 mmol, 9 ml) is bubbled into the solution using a syringe. The reaction mixture is then incubated on an oil bath at 60° C. After 24 hours, heating is discontinued and the reaction mixture is diluted with pure water (10 ml) and extracted with ether (15 ml×4). The residue is purified by column chromatography (silica gel 2 g, ethyl acetate/hexane 20%) to provide 1-phenyl-3-heptanol (26.9 mg, 55%). 1H NMR revealed that the crude product comprised the alcohol/reduced compound/starting compound in a molar ratio of 56/28/16.

Workup

  1. customA reaction vessel (30 ml, a two-neck, eggplant type flask) is subjected to nitrogen gas
  2. custompurging
  3. customThe reaction mixture is then incubated on an oil bath at 60° C
  4. temperatureheating
  5. extractionextracted with ether (15 ml×4)
  6. customThe residue is purified by column chromatography (silica gel 2 g, ethyl acetate/hexane 20%)

Sources & evidence

ORD record
ord-2869e56480ff43d9b8c3e28a636a9aef
Source dataset
uspto-grants-2001_08
Patent number
US06271425B1

Reaction notes

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