Sodium borohydride → 1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol

HRID 1168900노트

반응식

HRID 1168900 반응식
[CH3:1][C:2]1[C:3]([C:16]([C:18]2C(C)=CC3C(C)(C)CCC(C)(C)C=3C=2)=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[C:3]([CH:16]([OH:17])[CH3:18])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 22990221HCID 22990221, 화합물2회

생성물 1

HCID 49833401-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

To a solution of 4.17 g (17.1 mmol) of methyl [3,5,5,8,8-pentamethyl(5,6,7,8-tetrahydronaphthalen-2-yl] ketone (Compound 10) in methanol at 0° C. was portionwise added 0.77 g (20.4 mmol) of sodium borohydride and the resulting suspension stirred at 0° C. for 4 hours. Solvent was removed in-vacuo and the resulting solid taken-up in water, acidified using 1N HCl, and extracted three times with ether. The ether extracts were washed with water, brine and dried (MgSO4). The solvent was removed in-vacuo and resulting residue purified using flash chromatography (SiO2, 10% ethyl acetate in hexanes) to give a single isomer: the title compound as a white solid.

후처리

  1. customat 0° C.
  2. customSolvent was removed in-vacuo
  3. extractionextracted three times with ether
  4. washThe ether extracts were washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in-vacuo
  7. customresulting residue
  8. custompurified
  9. customto give a single isomer

출처 및 근거

ORD 기록
ord-8eb0c8b3607c4cf9aee64ecac79633f9
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627652B1

반응 노트

불러오는 중…