Borane → 3-Pyridinehexanol

HRID 1583419노트

반응식

HRID 1583419 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=[O:13])[CH:2]=1.B>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:2]=1

참가 물질

4

반응물 2

HCID 6331BoraneHCID 129045606-(Pyridin-3-yl)hexanoic acid

생성물 1

HCID 36861733-Pyridinehexanol수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 26.6 g of 3-pyridinehexanoic acid in 200 ml of dry tetrahydrofuran was cooled in an ice bath as 488 ml of 1 molar borane in tetrahydrofuran was added slowly. The reaction mixture was gradually brought to reflux temperature and was heated overnight. The excess reagent was quenched by the careful addition of 100 ml of methanol and the mixture was concentrated. The residue was diluted with excess 6N hydrochloric acid, allowed to stand overnight, made basic with 50% sodium hydroxide, and extracted with dichloromethane. The combined organic layers were dried over potassium carbonate, and evaporated to an oil which was distilled to give 22.6 g (92%) of 6-(3-pyridyl)hexanol, bp 180°-200° C./0.2 mm.

후처리

  1. additionwas added slowly
  2. temperatureto reflux temperature
  3. temperaturewas heated overnight
  4. customThe excess reagent was quenched by the careful addition of 100 ml of methanol
  5. concentrationthe mixture was concentrated
  6. additionThe residue was diluted with excess 6N hydrochloric acid
  7. extractionextracted with dichloromethane
  8. dry with materialThe combined organic layers were dried over potassium carbonate
  9. customevaporated to an oil which
  10. distillationwas distilled

출처 및 근거

ORD 기록
ord-d02628c9675349e59934a48d96ffb0c2
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04551460

반응 노트

불러오는 중…