Diethylamine → Tetrahydrofuran

HRID 1726004Notes

Reaction equation

HRID 1726004 reaction equation
CC1C=CC(S([O:11][CH2:12][CH2:13][C:14]#[CH:15])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23]>C1COCC1>[CH2:22]([N:24]([CH2:25][CH3:26])[CH2:12][CH2:13][C:14]#[CH:15])[CH3:23].[CH2:14]1[CH2:15][O:11][CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 2720203-Butynyl p-toluenesulfonate

Product 2

HCID 8028TetrahydrofuranYield 287.1%HCID 12225176(But-3-yn-1-yl)diethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-butynyl 4-methylbenzenesulfonate (10 mL, 57 mmol), K2CO3 (7.9 g, 57 mmol), and diethylamine (23.5 mL, 228 mmol) in 100 mL of THF was heated to reflux for 31 hours, cooled to room temperature, and filtered. The filtrate was concentrated under vacuum at a distillation temperature of 60° C. to provide 11.2 g of a 53 wt % solution of the desired product in THF (5.9 g assay, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ 0.93 (t, J=7.07 Hz, 6H) 2.21 (m, 2H) 2.44 (q, J=7.04 Hz, 4H) 2.55 (m, 2H) 2.72 (t, J=2.68 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 31 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under vacuum at a distillation temperature of 60° C.

Sources & evidence

ORD record
ord-70b547921c8e48cf85b21fd40dd264fc
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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