Diethylene Glycol → HCID 59411765, compound

HRID 1056467Notes

Reaction equation

HRID 1056467 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C[N+]1([O-])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[CH2:17]([OH:23])[CH2:18][O:19][CH2:20][CH2:21][OH:22].O.C1(C)C=CC(S(O)(=O)=[O:32])=CC=1>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([O:23][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22])[O:8][CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:32]

Participants

7

Reactant 4

HCID 8117Diethylene GlycolHCID 779706-Bromo-1-hexanolHCID 82029Methyl morpholine oxideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 59411765HCID 59411765, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The above procedure was carried out using the following quantities: 1-bromohexan-6-ol (1.76 g, 10.3 mmol), NMO (1.33 g, 11.3 mmol), molecular sieves (3.0 g), dichloromethane (40 mL), TPAP (0.37 g, 1.03 mmol); diethylene glycol (4.63 mL, 51.5 mmol), p-toluenesulfonic acid monohydrate (0.59 g, 3.90 mmol), molecular sieves (4.0 g) and dichloromethane (50 mL). Purification by flash chromatography on silica (gradient; dichloromethane to 5% methanol in dichlorometane) afforded the titled compound as a pale yellow oil (0.45 g, 12%).

Workup

  1. customPurification by flash chromatography on silica (gradient; dichloromethane to 5% methanol in dichlorometane)

Sources & evidence

ORD record
ord-42a8bf866beb449ca52ef05abc15d98c
Source dataset
uspto-grants-2016_07
Patent number
US09399016B2

Reaction notes

Loading…