Hexane → HCID 71307795, compound

HRID 926269Notes

Reaction equation

HRID 926269 reaction equation
[CH3:1][C:2]1[O:6][CH:5]=[N:4][CH:3]=1.[Li]CCCC.CCCCCC.[Sn:18](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22]>CCOCC>[CH3:1][C:2]1[O:6][C:5]([Sn:18]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:19][CH2:20][CH2:21][CH3:22])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 5284115-MethyloxazoleHCID 178418339Butyllithium

Product 1

HCID 71307795HCID 71307795, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 5-methyloxazole (5.0 g, 60.2 mmol) in Et2O (100 mL) was cooled to −78° C. under N2 and treated with a 1.6 M solution of BuLi in hexane (41.4 mL, 66.2 mmol) dropwise. The mixture was stirred at −78° C. for 30 min and a solution of Bu3SnCl (16.31 mL, 60.2 mmol) in Et2O (50 mL) was then added dropwise. The mixture was stirred at −78° C. for another 30 min and then allowed to warm to RT. The reaction mixture was filtered on celite, and the filtrate concentrated in vacuo. Purification by distillation (0.1 Torr, 128-130° C.) afforded the title compound (3.5 g) as a yellow liquid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.88 (m, 12 H) 1.14-1.22 (m, 6 H) 1.27-1.38 (m, 6 H) 1.52-1.61 (m, 6 H) 2.17-2.21 (m, 3 H) 7.49-7.54 (m, 1 H).

Workup

  1. stirringThe mixture was stirred at −78° C. for another 30 min
  2. temperatureto warm to RT
  3. filtrationThe reaction mixture was filtered on celite
  4. concentrationthe filtrate concentrated in vacuo
  5. customPurification
  6. distillationby distillation (0.1 Torr, 128-130° C.)

Sources & evidence

ORD record
ord-54939856f0c34db8b384b3594771bb91
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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