Sodium Hydroxide → (E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2, 1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid

HRID 2377316Notes

Reaction equation

HRID 2377316 reaction equation
C([O:3][C:4](=[O:33])/[C:5](/[CH3:32])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[C:17]([CH:29]3[CH2:31][CH2:30]3)[C:18]3[O:25][C:22]4([CH2:24][CH2:23]4)[C:21]([CH3:26])=[C:20]([CH3:27])[C:19]=3[CH:28]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH:29]1([C:17]2[C:18]3[O:25][C:22]4([CH2:24][CH2:23]4)[C:21]([CH3:26])=[C:20]([CH3:27])[C:19]=3[CH:28]=[C:15]([C:14]#[C:13][C:10]3[CH:9]=[CH:8][C:7](/[CH:6]=[C:5](\[CH3:32])/[C:4]([OH:33])=[O:3])=[CH:12][CH:11]=3)[CH:16]=2)[CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69069630(E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester2×

Product 1

HCID 21107275(E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2, 1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A solution of (E)-3-{4-[8-cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester (Intermediate 3, 0.06 g, 0.13 mmol) in ethanol (2 mL) was treated with a 1M solution of sodium hydroxide (0.5 mL, 0.5 mmol) and the resulting reaction mixture was heated at 55° C. for 4 h. The reaction mixture was cooled to ambient temperature and the volatiles were evaporated in vacuo to a residue that was neutralized with 5% hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a yellow solid after flash column chromatography over silica gel (230-400 mesh) (0.044 g, 82%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customthe volatiles were evaporated in vacuo to a residue that
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5e71923e8b584e9c8867a51b023d75ef
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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