(R)-(4-azido-3,4-dihydro-2H-chromen-7-yl)methanol → (R)-4-azido-3,4-dihydro-2H-chromene-7-carbaldehyde

HRID 2219878Notes

Reaction equation

HRID 2219878 reaction equation
[N:1]([C@H:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][OH:15])=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+:2]=[N-:3]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[N:1]([C@H:4]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]=[O:15])=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 1

HCID 59771815(R)-(4-azido-3,4-dihydro-2H-chromen-7-yl)methanol

Product 1

HCID 86604856(R)-4-azido-3,4-dihydro-2H-chromene-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-(4-azido-3,4-dihydro-2H-chromen-7-yl)methanol (3.293 g, 16.05 mmol) in 50 mL DCM was added manganese dioxide (160.3 mmol, 10.0 eq). The reaction mixture was allowed to stir overnight. A second portion of manganese dioxide (57.84 mmol, 3.5 eq) was added and stirred an additional 4 h. The reaction mixture was filtered and concentrated to yield the aldehyde.

Workup

  1. stirringstirred an additional 4 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-08fd58960f474befa20f83b305fa3f18
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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