Tetrabutylammonium Fluoride → HCID 86754884, compound

HRID 1604833Notes

Reaction equation

HRID 1604833 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][CH2:17][CH2:16][C@@:15]2([CH3:19])[C@H:10]1[CH2:11][CH2:12][CH2:13][C@@H:14]2[C@H:20]([CH3:30])[CH2:21]/[CH:22]=[CH:23]/[CH:24]=[CH:25]/[C:26]([CH3:29])([OH:28])[CH3:27])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[OH:28][C:26]([CH3:27])([CH3:29])/[CH:25]=[CH:24]/[CH:23]=[CH:22]/[CH2:21][C@H:20]([C@H:14]1[CH2:13][CH2:12][CH2:11][C@@H:10]2[C@:15]1([CH3:19])[CH2:16][CH2:17][CH2:18][C@@H:9]2[OH:8])[CH3:30]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86754885HCID 86754885, compound

Product 1

HCID 86754884HCID 86754884, compoundYield 97.4%

Procedure

954 mg of (3E,5E)-(R)-8-[(1R,4aR,5S,8aR)-5-(tert-butyldimethylsilanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-2-methyl-nona-3,5-dien-2-ol were treated with 10 equivalents of anhydr. TBAF (2 M in THF) at 55° for 24 h. The reaction mixture was poured onto crushed ice/NH4Cl, extracted with ether, washed with water and brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) yielded 685 mg of (1S,4aR,5R,8aR)-5-((3E,5E)-(R)-7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)-4a-methyl-decahydro-naphthalen-1-ol as pale-yellow oil.

Workup

  1. additionThe reaction mixture was poured
  2. extractionextracted with ether
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-a31f325af7e042b4954fde8311695751
Source dataset
uspto-grants-1999_11
Patent number
US05994569

Reaction notes

Loading…