Triethylborane → HCID 53652154, compound

HRID 1608398Notes

Reaction equation

HRID 1608398 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[C:9]([N:23]2[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:26][N:25]=[N:24]2)[CH:10]=[CH:11][CH:12]([OH:22])[CH2:13][C:14](=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][CH:3]=1.C(B(CC)CC)C.[BH4-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[C:9]([N:23]2[C:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[N:26][N:25]=[N:24]2)[CH:10]=[CH:11][CH:12]([OH:22])[CH2:13][CH:14]([OH:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7357TriethylboraneHCID 4311764Sodium borohydrideHCID 53685369HCID 53685369, compound

Product 1

HCID 53652154HCID 53652154, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 0.9 g (1.7 mmoles) of ethyl 9,9-bis(4-fluorophenyl)-5-hydroxy-8-(5-phenyl-1H-tetrazol-1-yl)-3-oxo-6,8-nonadienoate in 20 mL of dry tetrahydrofuran at 0° C. under argon was treated with triethylborane (1.74 mL, 1.0M in THF, 1.74 mmoles). The colorless solution was allowed to stir at 0° C. for 1.5 hours then cooled to -80° C. under argon. To this stirring solution was added sodium borohydride (130 mg, 3.4 mmoles) in one portion and the suspension was stirred for one hour. The crude reaction was quenched with 4.0 mL of 2M HCl followed by 20 mL of half saturated aqueous NH4Cl solution. The mixture was extracted twice with ethyl acetate (40 mL) and the organic layers were combined and evaporated. The concentrated crude product was diluted with 250 mL of methanol and the solution was allowed to stand at room temperature for 45 minutes then concentrated under reduced pressure at room temperature. Analytical TLC showed only one spot for the product. A solution of the crude product was filtered through silica gel and the filtrate was then concentrated under reduced pressure. Recrystallization from a mixture of ethyl acetate-hexanes gave 0.9 g of the title compound; m.p.=160.5°-161.5° C.

Workup

  1. temperaturethen cooled to -80° C. under argon
  2. stirringthe suspension was stirred for one hour
  3. customThe crude reaction
  4. customwas quenched with 4.0 mL of 2M HCl
  5. extractionThe mixture was extracted twice with ethyl acetate (40 mL)
  6. customevaporated
  7. concentrationThe concentrated crude product
  8. additionwas diluted with 250 mL of methanol
  9. waitto stand at room temperature for 45 minutes
  10. concentrationthen concentrated under reduced pressure at room temperature
  11. filtrationA solution of the crude product was filtered through silica gel
  12. concentrationthe filtrate was then concentrated under reduced pressure
  13. customRecrystallization
  14. additionfrom a mixture of ethyl acetate-hexanes

Sources & evidence

ORD record
ord-8d09de29d1b342d4a3c14ca65e1a4702
Source dataset
uspto-grants-1989_09
Patent number
US04870187

Reaction notes

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