Lithium tri-s-butylborohydride → HCID 178520419, compound

HRID 1458341Notes

Reaction equation

HRID 1458341 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:14]=[CH:13][C:9]2[NH:10][CH:11]=[N:12][C:8]=2[CH:7]=1.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+]>O1CCCC1>[NH:10]1[C:9]2[CH:13]=[CH:14][C:6]([CH:5]=[CH:4][CH2:3][OH:2])=[CH:7][C:8]=2[N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 178499690HCID 178499690, compound

Product 1

HCID 178520419HCID 178520419, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-(1H-benzoimidazol-5-yl)-acrylic acid methyl ester (50 mg in 1 mL dry tetrahydrofuran) at -78° C. was added 1.24 nL of a 1M solution of lithium tri-sec-butylborohydride in tetrahydrofuran and the mixture stirred at -78° C. for 4 hours followed by warming to -40° C. for an additional 4 hours. The reaction was quenched by addition of aqueous methanol, concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol, 87:13) to give the title compound (44 mg).

Workup

  1. temperatureby warming to -40° C. for an additional 4 hours
  2. customThe reaction was quenched by addition of aqueous methanol
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography on silica gel (methylene chloride:methanol, 87:13)

Sources & evidence

ORD record
ord-45a60625afd340969b5cc829b6947b73
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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