Water → HCID 22953576, compound

HRID 1992859Notes

Reaction equation

HRID 1992859 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br.[C:11](Cl)(=[O:15])[CH:12]([CH3:14])[CH3:13].O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn]>[CH3:13][CH:12]([CH3:14])[C:11](=[O:15])[CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

7

Reactant 3

HCID 962WaterHCID 62325Isobutyryl chlorideHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 22953576HCID 22953576, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred suspension of Pd(PPh3)2Cl2 (0.86 g, 1.22 mmol) and zinc powder (3.19 g, 48.8 mmol) in 1,2-dimethoxyethane (DME, 100 mL) at room temperature was slowly added a solution of 3-methoxybenzyl bromide (5.0 g, 24.4 mmol) and isobutyryl chloride in DME (25 mL). The mixture was stirred at room temperature for 1 h. Water was added, and the mixture was extracted with ether. The combined ether extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a brown oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (20:1) to give 3.03 g (64) of compound (§4 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.09 (d, J=7.0 Hz, 6H), 2.70-2.75 (m, 1H), 3.70 (s, 2H), 3.79 (s, 3H), 6.70-6.85 (m, 3H), 7.23 (t, J=8.0 Hz, 1H).

Workup

  1. extractionthe mixture was extracted with ether
  2. extractionThe combined ether extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give the crude product as a brown oil
  8. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (20:1)

Sources & evidence

ORD record
ord-585ae436cc954b039da88c1522539183
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…