Diethylene Glycol → HCID 59411746, compound

HRID 1056466Notes

Reaction equation

HRID 1056466 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].C[N+]1([O-])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH2:15]([OH:21])[CH2:16][O:17][CH2:18][CH2:19][OH:20].O.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH:5]([O:21][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20])[O:6][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:30]

Participants

7

Reactant 4

HCID 8117Diethylene GlycolHCID 82029Methyl morpholine oxideHCID 1183884-BromobutanolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 59411746HCID 59411746, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The above procedure was carried out using the following quantities: 1-bromobutan-4-ol (1.70 g, 11.1 mmol), NMO (1.47 g, 12.1 mmol), molecular sieves (3.30 g), dichloromethane (45 mL), TPAP (0.39 g, 1.11 mmol); diethylene glycol (3.99 mL, 44.4 mmol), p-toluenesulfonic acid monohydrate (0.64 g, 3.35 mmol), molecular sieves (4.40 g) and dichloromethane (50 mL). Purification by chromatography on neutral alumina (gradient; dichloromethane to 2% methanol in dichloromethane) afforded the titled compound as a pale yellow oil (0.68 g, 40%).

Workup

  1. customPurification by chromatography on neutral alumina (gradient; dichloromethane to 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d77632a530e044a1a05aad6be368b333
Source dataset
uspto-grants-2016_07
Patent number
US09399016B2

Reaction notes

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