Methyl morpholine oxide → HCID 86637814, compound

HRID 1881519Notes

Reaction equation

HRID 1881519 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)[CH3:5].C[N+]1([O-])CCOCC1>C(Cl)Cl>[CH3:5][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)[CH2:3][CH:2]=[O:1]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66705724HCID 66705724, compound

Product 1

HCID 86637814HCID 86637814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL one neck round bottom flask was added tert-butyl 4′-(3-hydroxy-1-methylpropyl)-biphenyl-2-carboxylate (197 mg, 0.604 mmol), N-methylmorpholine N-oxide (106 mg, 0.906 mmol), molecular sieves (300 mg) and methylene chloride (6 mL). The mixture was stirred while tetrabutyl ammonium ruthenate (21 mg, 0.0604 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 minutes, filtered through a stem of silica gel (5 g) and washed with mixture of ethyl acetate:hexanes (2:3). The filtrate was concentrated to afford tert-butyl 4′-(1-methyl-3-oxopropyl)biphenyl-2-carboxylate:

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. filtrationfiltered through a stem of silica gel (5 g)
  4. washwashed with mixture of ethyl acetate:hexanes (2:3)
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4c5bbf2e7ae048ff90e011111bd52dea
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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