Sodium borohydride → HCID 68154423, 화합물

HRID 73643노트

반응식

HRID 73643 반응식
[O:1]1[C@H:10]2[C:5](=[CH:6][CH2:7][CH2:8][C@H:9]2[CH:11]=[O:12])[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[O:1]1[C@H:10]2[C:5](=[CH:6][CH2:7][CH2:8][C@H:9]2[CH2:11][OH:12])[CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 86668663HCID 86668663, 화합물

생성물 1

HCID 68154423HCID 68154423, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

202 mg (8R,8aR)-3,4,6,7,8,8a-hexahydro-2H-chromene-8-carbaldehyde was dissolved in 8 mL MeOH and the solution was cooled to 0° C. and 52 mg sodium borohydride was added slowly. The reaction was stirred for several hours and gradually warmed to RT. The methanol was removed using a rotovap and the residue was diluted with CH2Cl2 and added to sat. NH4Cl. The mixture was separated, and the aqueous was extracted with CH2Cl2. The crude extract was dried over Na2SO4, filtered, concentrated, then purified on silica gel to provide the title compound. 1H NMR (400 MHz, CDCl3) δ=1.46-1.80 (m, 4H), 1.84-2.10 (m, 3H), 2.13-2.38 (m, 2H), 2.78-2.86 (m, 1H), 3.52-3.62 (m, 1H), 3.66-3.76 (m, 1H), 3.76-3.87 (m, 1H), 3.94-3.47 (m, 2H), 5.52 (s, 1H) ppm.

후처리

  1. temperaturegradually warmed to RT
  2. customThe methanol was removed
  3. additionthe residue was diluted with CH2Cl2
  4. additionadded to sat. NH4Cl
  5. customThe mixture was separated
  6. extractionthe aqueous was extracted with CH2Cl2
  7. extractionThe crude extract
  8. dry with materialwas dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified on silica gel

출처 및 근거

ORD 기록
ord-cc2ce523b11045a4a6f47a1b72679486
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829196B2

반응 노트

불러오는 중…