Benzyl Alcohol → HCID 59184663, compound

HRID 426145Notes

Reaction equation

[Na].Cl[C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([CH3:18])[CH:17]=2)[C:13]#[N:14])[C:6]([CH:19]([CH3:21])[CH3:20])=[C:5](Cl)[N:4]=1.[CH2:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([O:30][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([CH3:18])[CH:17]=2)[C:13]#[N:14])[C:6]([CH:19]([CH3:21])[CH3:20])=[C:5]([O:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:4]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Reactant 3

HCID 244Benzyl Alcohol

HCID 5360545Sodium

HCID 596868583-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzonitrile

Product 1

HCID 59184663HCID 59184663, compoundYield 68%

Procedure

Sodium (0.48 g, 21 mmol) was reacted with anhydrous benzyl alcohol (20 ml) under nitrogen at room temperature. The mixture was then cooled in an ice bath and (71) (3.22 g, 10 mmol) was added. After 1 hr., the mixture was stirred at room temperature for overnight. The mixture was evaporated in vacuo and the residue was dissolved in ether, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:9)) to afford 3.18 g (68%) of a colorless syrup. 1H NMR (200 MHz, CDCl3) δ 1.28 (6H, d, J=7.2 Hz), 2.39 (3H, s), 3.40 (1H, m), 5.14 (2H, s), 5.42 (2H, s), 7.13-7.44 (13H, m).

Workup

temperatureThe mixture was then cooled in an ice bath
customThe mixture was evaporated in vacuo
dissolutionthe residue was dissolved in ether
washwashed with water
dry with materialdried with anhydrous magnesium sulfate
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:9))

Sources & evidence

ORD record: ord-c43b0ed72a1e48e5b6df2b22da590dd6
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106064B2

Reaction notes

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