Hydrochloric Acid → HCID 57757225, compound

HRID 2100160Notes

Reaction equation

HRID 2100160 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[C:21]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C1COCC1.CCO>[C:21]1(=[C:13]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:28])=[O:3])=[CH:8][CH:9]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86613511HCID 86613511, compound

Product 1

HCID 57757225HCID 57757225, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl({4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}oxy)acetate (190) (0.20 g, 0.53 mmol) was dissolved in THF and EtOH (1:1, 6 mL). To the above solution was added 1 N NaOH (2.5 mL) at room temperature. The reaction was heated at 70° C. with stirring for 0.5 h and then cooled at RT. Reaction mixture was acidified with 20% aqueous HCl, and then extracted with EtOAc. The organic layer washed with brine, dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by flash column chromatography with chloroform and methanol (9:1 to 4:1) as an eluent to give 0.182 g of compound 191 as an off-white solid. mp 170-171° C. 1H NMR (300 MHz, DMSO-d6): δ 12.92 (s, 1H), 9.25 (s, 1H), d, J=8.4 Hz, 2H), 6.89 (d, J=8.4 Hz, 2H), 6.81 (d, J=8.7 Hz, 2H), 6.66 (d, J=8.4 Hz, 2H), 4.62 (s, 2H), 2.22 (br s, 4H), 1.5 (br s, 8H). LCMS (ESI): m/z 375.08 (M+Na)+. Anal. Calcd for C22H24O4: C, 74.98; H, 6.86; Found: C, 73.05; H, 6.74.

Workup

  1. temperaturecooled at RT
  2. customReaction mixture
  3. extractionextracted with EtOAc
  4. washThe organic layer washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product
  8. customThe product was purified by flash column chromatography with chloroform and methanol (9:1 to 4:1) as an eluent

Sources & evidence

ORD record
ord-08b78c0a8031483cae45aa788a23437c
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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