Diethylene Glycol → HCID 59411758, compound

HRID 1056468Notes

Reaction equation

HRID 1056468 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].C[N+]1([O-])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[CH2:19]([OH:25])[CH2:20][O:21][CH2:22][CH2:23][OH:24].O.C1(C)C=CC(S(O)(=O)=[O:34])=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][CH2:7][CH2:8][CH:9]([O:25][CH2:19][CH2:20][O:21][CH2:22][CH2:23][OH:24])[O:10][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:34]

Participants

7

Reactant 4

HCID 8117Diethylene GlycolHCID 82029Methyl morpholine oxideHCID 1626071-Octanol, 8-bromo-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 59411758HCID 59411758, compoundYield 128.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The above procedure was carried out using the following quantities: 1-bromooctan-8-ol (2 g, 9.57 mmol), NMO (1.12 g, 9.57 mmol), molecular sieves (3.0 g), dichloromethane (40 mL), TPAP (0.34 g, 0.96 mmol); diethylene glycol (5.18 mL, 57.6 mmol), p-toluenesulfonic acid monohydrate (0.55 g, 2.91 mmol), molecular sieves (4.0 g) and dichloromethane (40 mL). Purification by flash chromatography on silica (gradient; dichloromethane to 3% methanol in dichlorometane) afforded the titled compound as colourless oil (1.50 g, 39%).

Workup

  1. customPurification by flash chromatography on silica (gradient; dichloromethane to 3% methanol in dichlorometane)

Sources & evidence

ORD record
ord-a0a65c77350e419d83d1bd6de289e754
Source dataset
uspto-grants-2016_07
Patent number
US09399016B2

Reaction notes

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