Water → HCID 68180718, compound

HRID 2276913Notes

Reaction equation

HRID 2276913 reaction equation
C([Li])CCC.[CH3:6][C:7]1([CH3:23])[O:11][CH:10]([CH2:12][O:13][C:14]2[CH:22]=[CH:21][C:17]3[CH:18]=[CH:19][S:20][C:16]=3[CH:15]=2)[CH2:9][O:8]1.[B:24](OC(C)C)([O:29]C(C)C)[O:25]C(C)C.O>CCCCCC.O1CCCC1>[CH3:6][C:7]1([CH3:23])[O:11][CH:10]([CH2:12][O:13][C:14]2[CH:22]=[CH:21][C:17]3[CH:18]=[C:19]([B:24]([OH:29])[OH:25])[S:20][C:16]=3[CH:15]=2)[CH2:9][O:8]1

Participants

7

Reactant 4

HCID 962WaterHCID 21531Triisopropyl borateHCID 68180680HCID 68180680, compoundHCID 178418339Butyllithium

Product 1

HCID 68180718HCID 68180718, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

2.5 M n-butyllithium (1.75 mL, 4.37 mmol) in hexane was slowly added to 6-[(R/S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyloxy]benzothiophene ((R/S)-25, 1.05 g, 3.97 mmol) obtained in step 1 dissolved in anhydrous tetrahydrofuran (150 mL) at −78° C. under nitrogen atmosphere. 15 Minutes later, the resulting mixture was agitated at room temperature for 1 hour. After cooling again to −78° C., triisopropyl borate ((i-PrO)3B; 1.10 mL, 4.77 mmol) was slowly added. 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 drying with sodium sulfate, column chromatography yielded the target compound 6-[(R/S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyloxy]benzothiophene-2-boronic acid ((R/S)-26, 880 mg, 72%).

Workup

  1. customobtained in step 1
  2. temperatureAfter cooling again to −78° C.
  3. temperatureAfter slowly heating to room temperature
  4. stirringagitating for 3 hours
  5. customto quench
  6. customthe reaction
  7. extractionAfter extracting the organic compound with ethyl acetate
  8. dry with materialdrying with sodium sulfate, column chromatography

Sources & evidence

ORD record
ord-47c8a718bfa24d29878ed56b82d5fbb4
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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