3,3-Dimethylglutaric anhydride → HCID 59511945, compound

HRID 1157666Notes

Reaction equation

HRID 1157666 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][C:7](=[O:9])[O:6][C:4](=[O:5])[CH2:3]1.[CH2:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[C:17]([O:20]CC)(=[O:19])C>O1CCCC1>[O:19]1[C:12]2[CH:13]=[CH:14][C:15]([C:7](=[O:9])[CH2:8][C:2]([CH3:1])([CH3:10])[CH2:3][C:4]([OH:6])=[O:5])=[CH:16][C:11]=2[O:20][CH2:17]1

Participants

4

Reactant 2

HCID 778133,3-Dimethylglutaric anhydrideHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 59511945HCID 59511945, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of 3,3-dimethylglutaric anhydride (5.16 g, 36.3 mmol) in tetrahydrofuran to about 0° C. using an ice water bath. Add 3,4-(methlyeneoxy)phenylmagnesium bromide (1M solution in tetrahydrofuran, 40 mL, 40.0 mmol) quickly under a flow of nitrogen gas. Stir for 30 min, then allow to warm to room temperature over a period of 1 h. Quench with saturated ammonium chloride solution. Dilute with water and ethyl acetate, separate the aqueous layer (pH=8-9) and then acidify using 1N HCl (pH=4-5). Extract using ethyl acetate, dry with magnesium sulfate, filter, and concentrate to afford the crude title compound as an orange/yellow oil (5.99 g). Subject the crude residue to flash chromatography (RediSep silica gel columns (120 g), gradient of 100:0 to 75:25 cyclohexane/ethyl acetate) to obtain 1.80 g (19%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.58-7.61 (m, 1H), 7.45 (s, 1H), 6.82-6.87 (m, 1H), 6.05 (s, 2H), 3.00 (s, 2H), 2.52 (s, 2H) and 1.15 (s, 6H).

Workup

  1. customQuench with saturated ammonium chloride solution
  2. additionDilute with water and ethyl acetate
  3. customseparate the aqueous layer (pH=8-9)
  4. extractionExtract
  5. dry with materialdry with magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto afford the crude title compound as an orange/yellow oil (5.99 g)

Sources & evidence

ORD record
ord-a3447ea847e044a3bc307af455774531
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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