Hydrochloric Acid → HCID 12017643, compound

HRID 613314Notes

Reaction equation

HRID 613314 reaction equation
[CH3:1][C:2]1([CH3:41])[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][Si](CC(CC)CC)(C)C)[CH:13]=2)[C:8]2[CH:7]=[C:6]([C:28]#[C:29][C:30]3[CH:40]=[CH:39][C:33]([C:34]([O:36]CC)=[O:35])=[CH:32][CH:31]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+].Cl>CCO.C1COCC1>[CH3:1][C:2]1([CH3:41])[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[C:8]2[CH:7]=[C:6]([C:28]#[C:29][C:30]3[CH:31]=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:39][CH:40]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21998594HCID 21998594, compound2×

Product 1

HCID 12017643HCID 12017643, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(3-((2,2-dimethylethyl)-dimethylsiloxy)phenyl)-2-naphthalenyl)ethynyl]benzoate (Compound H) 40.0 mg (0.076 mmol) in 3 ml of EtOH and 2 ml of THF was added 40.0 mg (1.00 mmol, 1.00 ml) of NaOH (1.0 M aqueous solution). The solution was heated to 50° C. for 2 hours, cooled to room temperature, and acidified with 10% HCl. Extraction with EtOAc, followed by drying over Na2SO4, and removal of the solvents under reduced pressure afforded the title compound as a colorless solid. 1H NMR (d6-acetone): δ 7.90 (2H, d, J=8.3 Hz), 7.49 (2H, d, J=8.4 Hz), 7.35 (2H, s), 7.15-7.07 (2H, m), 6.77-6.69 (3H, m), 5.92 (1H, t, J=4.7 Hz), 2.25 (2H, d, J=4.7 Hz), 1.23 (6H, s).

Workup

  1. temperaturecooled to room temperature
  2. extractionExtraction with EtOAc
  3. dry with materialby drying over Na2SO4, and removal of the solvents under reduced pressure

Sources & evidence

ORD record
ord-008efb687ad94d8f897419a2baa95210
Source dataset
uspto-grants-1999_12
Patent number
US06008204

Reaction notes

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