Methyl morpholine oxide → HCID 86637814, compound

HRID 425434Notes

Reaction equation

HRID 425434 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-8d8fb6b63eb1483c8534fd3a4db1228e
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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