Methyl morpholine oxide → Ethyl 7-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)-6-formylheptanoate

HRID 1921879Notes

Reaction equation

HRID 1921879 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:32])[C:20]=1[O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH2:5][CH:6]([CH2:16][OH:17])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:32][C:19]1[CH:18]=[C:4]([CH2:5][CH:6]([CH:16]=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=[C:2]([F:1])[C:20]=1[O:21][Si:22]([CH:26]([CH3:27])[CH3:28])([CH:29]([CH3:31])[CH3:30])[CH:23]([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 57971930Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate

Product 1

HCID 57971915Ethyl 7-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)-6-formylheptanoate

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

1.19 g (2.52 mmol) of ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate are stirred with 5 g of 4 Å molecular sieves and 442 mg (3.78 mmol) of N-methylmorpholine N-oxide in 50 ml of dichloromethane at room temperature for 10 minutes. 44 mg (0.13 mmol) of tetrapropylammonium perruthenate are added, and the mixture is stirred at room temperature until reaction is complete. The mixture is filtered and the filtrate is washed with water and saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1). 1.0 g (84% of theory) of the title compound is obtained.

Workup

  1. filtrationThe mixture is filtered
  2. washthe filtrate is washed with water and saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-109de2df71b5486db9d65eb79205615a
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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