Acetic Acid → Borane;2-methylpyridine

HRID 425266

반응식

HRID 425266 반응식
[BH3:1].[N:2]1C=CC=CC=1.B.[CH2:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:10][CH3:11].[CH3:18][C:19]1[CH:20]=N[CH:22]=[CH:23][CH:24]=1.C(C1C=NC=CC=1)C.C(C1C=CN=CC=1)C.[C:41](O)(=O)[CH3:42]>N1C=CC=CC=1>[BH3:1].[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH3:9].[BH3:1].[CH2:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH3:10].[BH3:1].[N:13]1[C:12]([CH3:17])=[CH:9][CH:10]=[CH:11][C:41]=1[CH3:42].[BH3:1].[N:2]1[C:23]([CH3:22])=[CH:24][C:19]([CH3:18])=[CH:20][C:41]=1[CH3:42]

참가 물질

12

반응물 7

HCID 176Acetic AcidHCID 6331Borane2회HCID 79703-MethylpyridineHCID 108224-EthylpyridineHCID 108233-EthylpyridineHCID 693202-PropylpyridineHCID 2723995Borane;pyridine

생성물 4

HCID 16217944Borane;2-methylpyridineHCID 178419164HCID 178419164, 화합물HCID 178419168HCID 178419168, 화합물HCID 178419174HCID 178419174, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매2회

실험 절차

Pyridine forms an amine borane that is not moisture sensitive and very useful for reductive aminations and reductions in protic media. Pyridine borane is commercially available and often used in acetic acid to increase the reactivity of the borane. Unfortunately, it is thermally unstable and must be kept at temperatures less than 54° C. to avoid decomposition via hydroboration/polymerization processes. Its shelf-life at ambient temperature is only 6 months, Borane complexes of pyridine, 2-n-propylpyridine, 3-methylpyridine, 3-ethylpyridine and 4-ethylpyridine are liquids which violently decompose upon distillation (Mooney E. F. et al., J. Inorg. Nucl. Chem 1968, 30, p. 1439). 2-Picoline borane (mp. 50° C.), 2-ethylpyridine borane (mp, 50-51° C.), 2,6-lutidine borane (mp. 106-107° C.) and 2,4,6-collidine borane (mp. 99-100° C.) have been isolated as solids.

후처리

  1. custommust be kept at temperatures less than 54° C.
  2. customvia hydroboration/polymerization processes
  3. waitIts shelf-life at ambient temperature is only 6 months
  4. distillationupon distillation (Mooney E. F. et al., J. Inorg. Nucl. Chem 1968, 30, p. 1439)

출처 및 근거

ORD 기록
ord-4d143ad01d254d1b85140b1240a70419
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106200B2

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