Sodium Hydroxide → (2R)-2-{[(9Z,12Z)-octadeca-9,12-dien-1-yloxy]methyl}oxirane

HRID 573517Notes

Reaction equation

HRID 573517 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[Na+].[CH2:22]([C@H:24]1[O:26][CH2:25]1)Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[CH2:1]([O:19][CH2:22][C@H:24]1[CH2:25][O:26]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 149428(+)-EpichlorohydrinHCID 5365682Linoleyl alcohol

Product 1

HCID 58434808(2R)-2-{[(9Z,12Z)-octadeca-9,12-dien-1-yloxy]methyl}oxirane

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8058HexaneSolvent

Procedure

A 250 mL rb flask was charged with magnetic stirbar, tetrabutyl ammonium bromide (TBAB, 2.72 g, 8.4 mmol), linoleyl alcohol (225 g, 884 mmol), and sodium hydroxide (50.7 g, 1.2 mol), then cooled in an ice bath. The (S)-epichlorohydrin (156 g, 1.69 mol) was added slowly over 2 hours and then warmed to ambient temperature and stirred overnight. 259 mL of hexane was added and allowed to stir for 15 mins, then mixture was filtered and organic layer was concentrated in vacuo. The product was purified using 0-10% ethyl acetate/hexane gradient on 330 g silica column to give (2R)-2-{[(9Z,12Z)-octadeca-9,12-dien-1-yloxy]methyl}oxirane. 1H NMR (CDCl3, 300 mHz) δ 0.90-0.86 (m, 3H), 1.29 (s, 16H), 1.55-1.64 (m, 2H), 2.00-2.07 (m, 4H), 2.58-2.61 (m, 1H), 2.74-2.80 (m, 3H), 3.12-3.15 (m, 1H) 3.34-3.52 (m, 3H), 3.67-3.72 (dd, J=12 Hz, 1H) 5.30-5.35 (m, 4H); HRMS (m+1) calcd 323.2872. Found 323.2951.

Workup

  1. temperaturecooled in an ice bath
  2. stirringto stir for 15 mins
  3. filtrationmixture was filtered
  4. concentrationorganic layer was concentrated in vacuo
  5. customThe product was purified

Sources & evidence

ORD record
ord-04ee70d0c608468d9f1dc110fcf30602
Source dataset
uspto-grants-2015_05
Patent number
US09029604B2

Reaction notes

Loading…