Diethyl Ether → HCID 12133344, compound

HRID 2414916Notes

Reaction equation

HRID 2414916 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]([O:19][CH3:20])=[O:18])[CH:7]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:9]=1[O:10]C)([CH3:3])[CH3:2].B(Br)(Br)Br.C(OCC)C.CCCCCC>ClCCl>[CH3:20][O:19][C:17](/[CH:16]=[CH:15]/[C:6]1[CH:7]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:9]([OH:10])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1)=[O:18]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 25134Boron tribromideHCID 69501695HCID 69501695, compound

Product 1

HCID 12133344HCID 12133344, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-(3,5-diisopropyl-4-methoxyphenyl)acrylate (610 mg) and boron tribromide (10 mL) were combined in dichloromethane (10 mL) and the mixture was allowed to stir at 0° C. for 5 hours. The reaction was quenched with water and extracted with dichloromethane. The organics were washed (brine), dried (sodium sulfate), filtered, and condensed. Chromatography, with ethyl ether:hexane (gradient 10:90 to 20:80) as the eluent, provided material that was recrystallized from hexane to give the title compound as a white solid (420 mg); 1H-NMR (CDCl3) δ=1.28 (d, 12H, CH(CH3)2), 3.16 (m, 2H, CH(CH3)2), 3.80 (S, 3H, OCH3), 5.10 (S, 1H, OH), 6.32 (d, 2H, CH═CH), 7.24 (S, 2H, Ar—H), 7.66 (d, 2H, CH═CH).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe organics were washed (brine)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customcondensed
  7. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-da6d8f2ece9b4c9f8e674797c3dc63d3
Source dataset
uspto-grants-2004_11
Patent number
US06815555B2

Reaction notes

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