HCID 18446948, compound → HCID 18446949, compound

HRID 1268930Notes

Reaction equation

HRID 1268930 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C@H:11]([CH2:13][CH3:14])[CH3:12])[CH:5]=[O:6].O.S(=O)(=O)(O)[OH:17]>CC(C)=O.[O-2].[Cr+6].[O-2].[O-2]>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C@H:11]([CH2:13][CH3:14])[CH3:12])[C:5]([OH:17])=[O:6]

Participants

5

Reactant 2

HCID 18446948HCID 18446948, compoundHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 18446949HCID 18446949, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A solution of 130 mg (0.66 mmol) of 3-fluoro-4-(2-(S)-butoxy)benzaldehyde in 1 mL of acetone was treated with a 73 mg (0.73 mmol) of chromium (VI) oxide in a 3:1 v/v mixture of water/sulfuric acid at 0° C. The reaction was allowed to warm to rt and was stirred for 2 hr then extracted with 10 mL of EtOAc, washed with brine, dried over MgSO4 and concentrated to afford 130 mg of the title compound: 1H NMR (500 Mhz) δ 1.00 (t, J=7.6, 3H), 1.36 (d, J=6.2, 3H), 1.70 (m, 1H), 1.82 (m, 1H), 4.44 (m, 1H), 6.99 (t, J=8.2, 1H), 7.79 (d, J=8.2, 1H), 7.85 (s, 1H).

Workup

  1. extractionthen extracted with 10 mL of EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d7eb6911ae5c4f29aa48760b7323330f
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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