Tetrahydrofuran → HCID 118233268, compound

HRID 1526669Notes

Reaction equation

HRID 1526669 reaction equation
[OH:1][C@@H:2]1[CH2:23][CH:22]2[C@:17]([CH3:24])([CH2:18][CH2:19][CH2:20][CH2:21]2)[C@@H:16]2[C@@H:3]1[C@H:4]1[C@:13]([CH3:26])([C@@H:14]([OH:25])[CH2:15]2)[C@@H:7]([C@H:8]([CH3:12])[CH2:9][CH2:10][CH3:11])[CH2:6][CH2:5]1.[H-].[Na+].[CH2:29](I)[CH:30]=[CH2:31].[CH2:33]1[CH2:37]OC[CH2:34]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:29]([O:1][C@@H:2]1[CH2:23][CH:22]2[C@:17]([CH3:24])([CH2:18][CH2:19][CH2:20][CH2:21]2)[C@@H:16]2[C@@H:3]1[C@H:4]1[C@:13]([CH3:26])([C@@H:14]([O:25][CH2:37][CH:33]=[CH2:34])[CH2:15]2)[C@@H:7]([C@H:8]([CH3:12])[CH2:9][CH2:10][CH3:11])[CH2:6][CH2:5]1)[CH:30]=[CH2:31]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 118233264HCID 118233264, compound

Product 1

HCID 118233268HCID 118233268, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

To a solution of dihydroxycholane 1 (4.0 g, 11.1 mmol) in 200 mL THF was added sodium hydride (4.42 g, 110.5 mmol) at 0° C. The reaction mixture was warmed up to room temperature and then stirred for 1 hour. Allyl iodide (9.23 g, 55.3 mmol) and tetrabutylammonium iodide (12.3 g, 33.2 mmol) were added to the reaction mixture which was then heated to reflux for overnight. The reaction was quenched with saturated NH4Cl solution at room temperature and then extracted with EtOAc. The combined organic layers were washed with brine and then dried over anhydrous Na2SO4. The filtered organic portion was concentrated under vacuum to give the product 2 (3.6 g, 74%) which was directly used for the next steps.

Workup

  1. temperaturewas then heated
  2. temperatureto reflux for overnight
  3. customThe reaction was quenched with saturated NH4Cl solution at room temperature
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationThe filtered organic portion was concentrated under vacuum

Sources & evidence

ORD record
ord-9641e6e98ed8443fa4de590f571e981a
Source dataset
uspto-grants-2015_07
Patent number
US09085602B1

Reaction notes

Loading…