HCID 86691458, compound → HCID 131731651, compound

HRID 1618862Notes

Reaction equation

HRID 1618862 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH:18]([CH3:20])[N:17]([CH3:21])[C:16]2=O)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:29]([Li])[CH3:30]>C1(C)C=CC=CC=1.C(=O)=O>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH:18]([CH3:20])[N:17]([CH3:21])[C:16]2=[CH:29][CH3:30])[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 86691458HCID 86691458, compoundHCID 178506846HCID 178506846, compound

Product 1

HCID 131731651HCID 131731651, compound

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

Product of Step 7 (2.5 g) was dissolved in toluene (150 mL). The solution was cooled by surrounding the flask with dry ice and the contents were stirred under argon purging for 30 min. To this was added a dispersion of ethyl lithium (25 mL, 1.7 M in butyl ether). The reaction mixture was stirred in dry ice under argon purging for 1 hr and allowed to warm to 25° C. The reaction mixture was stirred for 3 hr at 25° C. under argon purging. Then, the reaction mixture was poured in a beaker and cooled to 0° C. using an ice bath. The reaction was quenched by slow addition of water (5 mL) to the stirring toluene solution. After the evolution of gases ceased, the reaction mixture was extracted with water (three times at 50 mL each). The organic layer was diluted with ethyl acetate (500 mL) and dried over anhydrous magnesium sulfate. The organic layer was filtered and concentrated under vacuum to obtain Step 8 product as a red-brown viscous oil (3 mL). Mass spectrometry: m/z=408 (M+H). The product was carried forward without further purification.

Workup

  1. temperatureThe solution was cooled
  2. stirringThe reaction mixture was stirred for 3 hr at 25° C. under argon purging
  3. additionThen, the reaction mixture was poured in a beaker
  4. temperaturecooled to 0° C.
  5. customThe reaction was quenched by slow addition of water (5 mL) to the stirring toluene solution
  6. extractionthe reaction mixture was extracted with water (three times at 50 mL each)
  7. additionThe organic layer was diluted with ethyl acetate (500 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe organic layer was filtered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8c5382fa52e944fe9ce058849053cfc8
Source dataset
uspto-grants-2014_07
Patent number
US08771964B2

Reaction notes

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