(4-(2-(Tetrahydrofuran-2-yl)-ethyl)-phenyl)-methanol → 4-(2-(Tetrahydrofuran-2-yl)-ethyl)-benzaldehyde

HRID 1891752Notes

Reaction equation

HRID 1891752 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1>[O-2].[O-2].[Mn+4].C(OCC)(=O)C>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 59255503(4-(2-(Tetrahydrofuran-2-yl)-ethyl)-phenyl)-methanol

Product 1

HCID 592553414-(2-(Tetrahydrofuran-2-yl)-ethyl)-benzaldehydeYield 95.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an ethyl acetate (50 mL) solution of (4-(2-(tetrahydrofuran-2-yl)-ethyl)-phenyl)-methanol (600 mg, 2.91 mmol) described in Manufacturing Example 82-1-2 was added active manganese dioxide (10 g, 115 mmol), which was stirred for 12 hours at room temperature. The reaction liquid was suction filtered through a Celite pad, and washed with ethyl acetate (50 mL). The filtrate was concentrated under a reduced pressure to obtain the title compound (565 mg, 95%).

Workup

  1. customThe reaction liquid
  2. filtrationfiltered through a Celite pad
  3. washwashed with ethyl acetate (50 mL)
  4. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-8a0db25de2d945d69b0b935a153540e5
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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