Hydrochloric Acid → HCID 11474726, compound

HRID 229234Notes

Reaction equation

HRID 229234 reaction equation
C(OC([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[C:27]2[CH2:32][C:31]([CH3:34])([CH3:33])[CH2:30][C:29]([CH3:36])([CH3:35])[CH2:28]2)[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]([O:24]CC)=[O:23])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)=O)C.[OH-].[Na+].Cl>CCO.C1COCC1>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[C:27]2[CH2:28][C:29]([CH3:36])([CH3:35])[CH2:30][C:31]([CH3:34])([CH3:33])[CH2:32]2)[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]([OH:24])=[O:23])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68654271HCID 68654271, compound

Product 1

HCID 11474726HCID 11474726, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-{4-[(4-{[(ethyloxy)carbonyl]oxy}phenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-2-propynoate (148) (88 mg, 0.18 mmol) in a mixture of EtOH (4 mL) and THF (4 mL) was added an aqueous solution of 1 N NaOH (5 mL). The mixture was stirred at 60° C. for 2 h. Upon cooling, the mixture was acidified to pH=2 with an aqueous solution of 1 N HCl. The mixture was extracted with EtOAc (2×50 mL). The combined organic extract was washed with water, brine and dried over Na2SO4. Upon concentration and trituration with hot 1:1 hexanes/ether (contained 1% of methanol), (35 mg (50%) of compound 149 was obtained as white solid. mp 172-174° C. (dec.). 1H NMR (400 MHz, DMSO-d6): δ 0.86 (s, 6H), 0.87 (s, 6H), 1.24 (s, 2H), 1.85 (s, 2H), 1.91 (s, 2H), 6.66 (d, J=8.4 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 7.19 (d, J=8.1 Hz, 2H), 7.52 (d, J=8.1 Hz, 2H), 9.31 (s, 1H), 13.73 (s, 1H). HRMS (EI) Calcd for C32H44O3Si2: 532.2829 (M+.); Found: 532.1591.

Workup

  1. temperatureUpon cooling
  2. extractionThe mixture was extracted with EtOAc (2×50 mL)
  3. extractionThe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationUpon concentration and trituration with hot 1:1 hexanes/ether (contained 1% of methanol)

Sources & evidence

ORD record
ord-bd1418c804a34abd8e3302617e911780
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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