Hydrochloric Acid → HCID 11992770, compound

HRID 2241056Notes

Reaction equation

HRID 2241056 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][C:3]=1[O:25][CH2:26][C:27]([O:29]CC)=[O:28].[OH-].[Na+].C(O)C.Cl>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:9]2[CH2:14][C:13]([CH3:15])([CH3:16])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][C:3]=1[O:25][CH2:26][C:27]([OH:29])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86621473HCID 86621473, compound

Product 1

HCID 11992770HCID 11992770, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Compound 42 (50 mg, 0.12 mmol), NaOH (50 mg, 1.25 mmol), ethanol (5 mL) and water (500 uL) were combined in a sealed microwave vessel. The mixture was heated at 100° C. for 10 minutes in a Personal Chemistry Emrys Optimizer microwave. The reaction was then acidified with 1 N HCl (5 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over MgSO4, filtered, and the solvents removed in vacuuo to give 46 mg (98%) of 43 as a purple solid. 1H NMR (400 MHz, CDCl3): δ 0.88 (s, 6H), 0.91 (s, 6H), 1.20-1.25 (m, 5H), 1.75 (s, 2H), 1.90 (s, 2H), 2.23 (s, 3H), 4.61 (s, 2H), 6.74 (d, J=8.3 Hz, 1H), 6.75-7.05 (m, 2H), 7.09-7.15 (m, 3H) 7.25-7.36 (m, 2H).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents removed in vacuuo

Sources & evidence

ORD record
ord-572fc6f42fd8459ca06348851313608c
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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