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

HRID 1869832Notes

Reaction equation

HRID 1869832 reaction equation
C[O:2][C:3](=[O:31])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:15]=[C:16]([CH:28]3[CH2:30][CH2:29]3)[C:17]3[O:24][C:21]4([CH2:23][CH2:22]4)[CH2:20][C:19]([CH3:26])([CH3:25])[C:18]=3[CH:27]=2)=[CH:8][CH:7]=1)[CH3:5].[OH-].[Na+]>CO>[CH:28]1([C:16]2[C:17]3[O:24][C:21]4([CH2:23][CH2:22]4)[CH2:20][C:19]([CH3:25])([CH3:26])[C:18]=3[CH:27]=[C:14]([C:13]#[C:12][C:9]3[CH:8]=[CH:7][C:6]([CH:4]([CH3:5])[C:3]([OH:31])=[O:2])=[CH:11][CH:10]=3)[CH:15]=2)[CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 690752312-{4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-phenyl}-propionic acid methyl ester2×

Product 1

HCID 211071312-{4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2-{4-[(8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane]-6-yl)ethynyl]-phenyl}-propionic acid methyl ester (Intermediate 1, 0.072 g, 0.174 mmol) in methanol (5 mL) was treated with a 1M solution of sodium hydroxide (1 mL, 1 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 diluted with 10% hydrochloric acid till neutral 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 white solid after flash column chromatography over silica gel (230-400 mesh) (0.04 g, 57%).

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. additionwas diluted with 10% hydrochloric acid till neutral and
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-a932b2d1e1d540b390539452238f80a7
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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