Methyl morpholine oxide → 4-[3-(benzyloxy)-5-fluorophenyl]-4-formyl-3,4,5,6-tetrahydro-2H-pyran

HRID 1108069Notes

Reaction equation

HRID 1108069 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2([CH2:22][OH:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2([CH:22]=[O:23])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxide2×HCID 187863144-[3-(Benzyloxy)-5-fluorophenyl]-4-hydroxymethyl-3,4,5,6-tetrahydro-2H-pyran

Product 1

HCID 187863774-[3-(benzyloxy)-5-fluorophenyl]-4-formyl-3,4,5,6-tetrahydro-2H-pyranYield 86%

Reagents, catalysts & solvents 1

HCID 178419074HCID 178419074, compoundCatalyst2×

Procedure

Tetra-n-propylammonium perruthenate (70 mg, 0.2 mmol) was added in one portion to a stirred mixture of 4-[3-(benzyloxy)-5-fluorophenyl]-4-hydroxymethyl-3,4,5,6-tetrahydro-2H-pyran (1.28 g, 4.0 mmol), N-methylmorpholine N-oxide (0.70 g, 6.0 mmol) and powdered 3 Å molecular sieves (2.0 g) at room temperature under nitrogen atmosphere. After 20 min tetra-n-propylammonium perruthenate (30 mg, 0.085 mmol) and N-methylmorpholine N-oxide (0.30 g, 2.6 mmol) were added and stirring continued for 30 min. The mixture was chromatographed (silica-gel, 110 g: 25% ethyl acetate in n-hexane) to give the titled compound as a colorless liquid (1.08 g, 86%).

Workup

  1. customat room temperature
  2. customThe mixture was chromatographed (silica-gel, 110 g: 25% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-7a654aa85680489183b3c36a79523340
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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