Diisobutylaluminum hydride → HCID 89556341, compound

HRID 578880Notes

Reaction equation

HRID 578880 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[C:9]1([C:12]#[N:13])[CH2:11][CH2:10]1.CC(C[AlH]CC(C)C)C.[BH4-].[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[C:9]1([CH2:12][NH2:13])[CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 14487Diisobutylaluminum hydrideHCID 4311764Sodium borohydrideHCID 9855836Potassium sodium tartarateHCID 89544502HCID 89544502, compound

Product 1

HCID 89556341HCID 89556341, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
-10 °C

Procedure

1-(4,6-Dichloro-3-pyridyl)cyclopropanecarbonitrile (0.1 g, 0.469 mmol) was dissolved in Toluene (2.3 mL). At −10° C. DIBAL-H 1M in Toluene (0.98564 mL, 0.986 mmol) was added dropwise. The reaction mixture was stirred 30 min at −10° C. At −10° C. NaBH4 (0.10871 g, 2.816 mmol) was added, then carefully 3 mL MeOH. The reaction mixture was stirred 30 min at rt. It was poured into 25 ml of 1N potassium sodium tartrate. The pale yellow solution was extracted 3 times with Ether. The combined organic phases were washed with brine and dried with Na2SO4, filtrated and the filtrate evaporated. The product was obtained as a pale yellow oil (99 mg).

Workup

  1. customAt −10° C
  2. customAt −10° C
  3. stirringThe reaction mixture was stirred 30 min at rt
  4. extractionThe pale yellow solution was extracted 3 times with Ether
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltrated
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-04d8bf1bce4d45f7b1e5d985f6d6de7d
Source dataset
uspto-grants-2015_05
Patent number
US09040708B2

Reaction notes

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