Succinic anhydride → 4-(3-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}phenyl)-4-oxobutanoic acid

HRID 1986397Notes

Reaction equation

HRID 1986397 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[O:21]1[C:25](=[O:26])[CH2:24][CH2:23][C:22]1=[O:27]>C1COCC1.CCOC(C)=O>[CH3:13][C:12]([Si:9]([CH3:11])([CH3:10])[O:8][C:4]1[CH:3]=[C:2]([C:25](=[O:26])[CH2:24][CH2:23][C:22]([OH:27])=[O:21])[CH:7]=[CH:6][CH:5]=1)([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 11254705(3-Bromophenoxy)(tert-butyl)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 688720744-(3-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}phenyl)-4-oxobutanoic acidYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under argon, to a solution of [(3-bromophenyl)oxy](1,1-dimethylethyl)-dimethylsilane (1.5 g, 5.22 mmol) in THF (60 mL) at −78° C., was added dropwise n-BuLi (3.6 mL, 1.6 M in hexanes), 20 min after the addition, this solution was added to a solution of dihydro-2,5-furandione (630 mg, 6.26 mmol) in THF (10 mL) under argon at −78° C. 15 min later, the reaction mixture was slowly warmed to rt overnight. The reaction mixture was diluted with EtOAc (50 mL), then extracted with NaOH (20 ml, 1.0 N). Aquaous layer was acidified with HCl (1.0N) until pH=2, then extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound as a colorless crystal (546 mg, 54%). MS (ES+) m/e 195 [M+H]+.

Workup

  1. additionafter the addition
  2. extractionextracted with NaOH (20 ml, 1.0 N)
  3. extractionextracted with EtOAc (100 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-70d9f19a27c74194a90fc203fce4f55c
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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