Triisopropyl borate → HCID 17964037, compound

HRID 1375027Notes

Reaction equation

HRID 1375027 reaction equation
I[C:2]1[CH:3]=[C:4]([C:12]2[O:13][CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[B:19]([O:28]C(C)C)([O:24]C(C)C)[O:20]C(C)C.C([Li])CCC>O1CCCC1>[CH3:17][C:15]1([CH3:18])[CH2:14][O:13][C:12]([C:4]2[CH:3]=[C:2]([O:20][B:19]([OH:28])[OH:24])[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=2)=[N:16]1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 17963974HCID 17963974, compoundHCID 178418339Butyllithium

Product 1

HCID 17964037HCID 17964037, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-iodo-5-(trifluromethyl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole (2.11 g) and triisopropyl borate (1.26 g) in tetrahydrofuran (21 ml) was added dropwise butyllithium (1.6 M in hexane) at −70° C. After stirring for 4 hours, the mixture was quenched with 2N hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate, and evaporated in vacuo to give 3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-5-(trifluoromethyl)phenylboroic acid (1.65 g) as a yellow oil. This oil was used immediately in the next reaction without further purification because of its instability.

Workup

  1. customthe mixture was quenched with 2N hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-834d2c34f5a14ee4bfcb49ed2cdcf74d
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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