Tetrabutylammonium Fluoride Trihydrate → (1S,4aR,5R,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-decahydro-naphthalen-1-ol

HRID 581612노트

반응식

HRID 581612 반응식
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O.O.O.C([Si](C)(C)[O:27][C@H:28]1[CH2:37][CH2:36][CH2:35][C@@:34]2([CH3:38])[C@H:29]1[CH2:30][CH2:31][CH2:32][C@@H:33]2[C@H:39]([CH3:47])[CH2:40][C:41]#[C:42][C:43]([CH3:46])([OH:45])[CH3:44])(C)(C)C>C1COCC1>[OH:45][C:43]([CH3:44])([CH3:46])[C:42]#[C:41][CH2:40][C@H:39]([C@H:33]1[CH2:32][CH2:31][CH2:30][C@@H:29]2[C@:34]1([CH3:38])[CH2:35][CH2:36][CH2:37][C@@H:28]2[OH:27])[CH3:47]

참가 물질

4

반응물 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 57089693(R)-6-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-2-methyl-hept-3-yn-2-ol

생성물 1

HCID 57216772(1S,4aR,5R,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-decahydro-naphthalen-1-ol수율 87.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

12.0 g (38.0 mmol) of nBu4NF.3H2O in 40 ml of THF was carefully dried by stirring during 2 h at RT over 15 g of 3 Å molecular sieve. This solution was then added to 1.93 g (4.748 mmol) of (R)-6-[(1R,4aR,5S,8aR)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-2-methyl-hept-3-yn-2-ol and the mixture kept for 40 h at 55°. The reaction mixture was then poured onto crushed ice, extracted twice with ether, washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) afforded 1.22 g of the title compound as white crystals of mp. 134-135°.

후처리

  1. waitthe mixture kept for 40 h at 55°
  2. additionThe reaction mixture was then poured
  3. customonto crushed ice
  4. extractionextracted twice with ether
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-318a3761522c41a69f2029809f3024e3
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919986

반응 노트

불러오는 중…