Water → HCID 68180686, compound

HRID 2276902Notes

Reaction equation

HRID 2276902 reaction equation
C([Li])CCC.[Si:6]([O:13][C:14]1[CH:22]=[CH:21][C:17]2[CH:18]=[CH:19][S:20][C:16]=2[CH:15]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[B:23](OC(C)C)([O:28]C(C)C)[O:24]C(C)C.O>CCCCCC.O1CCCC1>[Si:6]([O:13][C:14]1[CH:22]=[CH:21][C:17]2[CH:18]=[C:19]([B:23]([OH:28])[OH:24])[S:20][C:16]=2[CH:15]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 21531Triisopropyl borateHCID 68180760HCID 68180760, compoundHCID 178418339Butyllithium

Product 1

HCID 68180686HCID 68180686, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

2.5 M n-butyllithium (23 mL, 57.5 mmol) in hexane was slowly added to the 6-(t-butyldimethylsilyloxy)benzothiophene (23, 13.6 g, 51.0 mmol) dissolved in anhydrous tetrahydrofuran (150 mL) at −78° C. under nitrogen atmosphere. 15 minutes later, the mixture was agitated at room temperature for 1 hour. After cooling again to −78° C., triisopropyl borate ((i-PrO)3B; 14.0 mL, 62.0 mmol) was slowly added. Then, after slowly heating to room temperature and agitating for 3 hours, water was added to quench the reaction. After extracting the organic compound with ethyl acetate and removing water using sodium sulfate, column chromatography yielded the target compound 6-(t-butyldimethylsilyloxy)benzothiophene-2-boronic acid (24, 9.75 g, 62%).

Workup

  1. temperatureAfter cooling again to −78° C.
  2. temperatureThen, after slowly heating to room temperature
  3. stirringagitating for 3 hours
  4. customto quench
  5. customthe reaction
  6. extractionAfter extracting the organic compound with ethyl acetate
  7. customremoving water

Sources & evidence

ORD record
ord-132c6aaebfcd4cd9923111f331819e81
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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