HCID 57812393, compound → HCID 57812302, compound

HRID 912026Notes

Reaction equation

HRID 912026 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([OH:15])[CH2:11][C:12]([CH3:14])=[CH2:13]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([OH:15])[CH2:11][CH:12]([CH3:13])[CH3:14]

Participants

4

Reactant 1

HCID 57812393HCID 57812393, compound

Product 1

HCID 57812302HCID 57812302, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2,6-dichloro-3-fluorophenyl)-3-methylbut-3-en-1-ol (0.95 mmol) in EtOAc (5.0 mL) was added palladium 10% wt on activated carbon (30 mg). The flask was evacuated and purged with hydrogen gas (3×) and allowed to stir under hydrogen for 2.5 h. The reaction mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure to give a light yellow oil. The material was purified by silica gel chromatography using Hexane/EtOAc (80:20) as eluent to obtain the desired product as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ=1.02 (dd, J=6.6, 4.5 Hz, 6H), 1.58 (ddd, J=13.9, 8.8, 4.5 Hz, 1H), 2.05-2.13 (m, 1H), 2.71 (d, J=10.1 Hz, 1H), 5.49 (td, J=10.0, 4.8 Hz, 1H), 7.03 (dd, J=8.8, 7.8 Hz, 1H), 7.27-7.29 (m, 1H).

Workup

  1. customThe flask was evacuated
  2. custompurged with hydrogen gas (3×)
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a light yellow oil
  6. customThe material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b2a6062f0510494daaaec997ad07d8b2
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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