1-Chloro-3-methyl-2-butene → HCID 22603010, compound

HRID 2307932Notes

Reaction equation

HRID 2307932 reaction equation
CO[C:3]1C=C(C)[C:6](CC2OC(C(OC)=O)=CC=2)=[C:5]([CH3:20])[CH:4]=1.[CH3:21][O:22][C:23]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[C:24]=1[CH2:25][C:26]1[O:30][C:29]([C:31]([O:33][CH3:34])=[O:32])=[CH:28][CH:27]=1.ClCC=C(C)C.CC(C)([O-])C.[K+].CC1C=C(OCCC(C)=C)C=C(C)C=1CC1OC(C(OC)=O)=CC=1>O.CS(C)=O>[CH3:40][C:35]1[CH:36]=[C:37]([CH3:39])[CH:38]=[C:23]([O:22][CH2:21][CH2:3][CH2:4][C:5]([CH3:20])=[CH2:6])[C:24]=1[CH2:25][C:26]1[O:30][C:29]([C:31]([O:33][CH3:34])=[O:32])=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 104291-Chloro-3-methyl-2-buteneHCID 22602995HCID 22602995, compoundHCID 22602999HCID 22602999, compoundHCID 22603014HCID 22603014, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22603010HCID 22603010, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

In a 500-mL round-bottom flask, a mixture of methyl 5-(4-methoxy-2,6-dimethylbenzyl)-2-furoate (202) and methyl 5-(2-methoxy-4,6-dimethylbenzyl)-2-furoate (203) (4.52 g, 17.38 mmol) and anhydrous DMSO (50 mL) were placed. To this solution, 1-chloro-3-methylbut-2-ene (1.91 g, 18.25 mmol) and potassium tert-butoxide (2.25 g, 20.07 mmol) were added. The reaction mixture was placed under nitrogen and stirred at room temperature for 3 hours. The reaction mixture was poured into, water and extracted with ethyl acetate. The separated organic layer-was washed with water (2×) and brine and dried over MgSO4 then concentrated to yield a mixture of methyl 5-{2,6-dimethyl-4-[(3-methylbut-3-enyl)oxy]benzyl}-2-furoate (204) and methyl 5-{2,4-dimethyl-6-[(4-methylpent-4-enyl)oxy]benzyl}-2-furoate (205) (3.64 g, 64% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer-was washed with water (2×) and brine
  3. dry with materialdried over MgSO4
  4. concentrationthen concentrated
  5. customto yield

Sources & evidence

ORD record
ord-2a48497d54364852a20e5249ba526e5f
Source dataset
uspto-grants-2004_12
Patent number
US06833372B2

Reaction notes

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