Pyridine → (2RS,3E,6R)-6,10-dimethyl-3,9-undecadien-2-ol acetate

HRID 1722096Notes

Reaction equation

HRID 1722096 reaction equation
N1C=CC=CC=1.[C:7]([O:10][C:11](=[O:13])[CH3:12])(=O)[CH3:8].[CH3:14][C@H:15]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH2:16]/[CH:17]=[CH:18]/C(O)C>>[C:11]([O:10][CH:7](/[CH:18]=[CH:17]/[CH2:16][C@H:15]([CH3:14])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH3:8])(=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13588614(2RS,3E,6R)-6,10-dimethyl-3,9-undecadien-2-ol

Product 1

HCID 14368740(2RS,3E,6R)-6,10-dimethyl-3,9-undecadien-2-ol acetateYield 99.1%

Conditions

Temperature
0 °C

Procedure

A flame-dried, 250 mL, three-necked flask containing a magnetic stirring bar was charged under argon with 7.9 g (8.1 mL, 0.10 mol) of dry pyridine. After cooling in an ice-bath, 10.2 g (9.4 mL, 0.10 mol) of acetic anhydride and then 10.0 g (0.051 mol) of (2RS,3E,6R)-6,10-dimethyl-3,9-undecadien-2-ol were added dropwise, and the reaction was stirred for 2 hours at 0° C. and then overnight at 20° C.. The reaction mixture was poured onto 2N HCl/ice and extracted with 2×200 mL of ether. The combined extracts were washed with 2N HCl, sat. NaHCO3 solution, and brine, dried over Na2SO4, filtered and evaporated. Kugelrohr distillation at ca. 105°-130° C./0.1 mmHg afforded 12.05 g (99%) of (2RS,3E,6R)-6,10-dimethyl-3,9-undecadien-2-ol acetate as colorless liquid. Calcd. for C15H26O 2 (238.4): C, 75.58; H, 10.99; Found: C, 75.47; H, 11.04%. [α]D25 =2.16° (2.04% in CHCl3).

Workup

  1. additionA flame-dried, 250 mL, three-necked flask containing a magnetic stirring bar
  2. temperatureAfter cooling in an ice-bath
  3. customovernight
  4. customat 20° C.
  5. extractionextracted with 2×200 mL of ether
  6. washThe combined extracts were washed with 2N HCl, sat. NaHCO3 solution, and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. distillationKugelrohr distillation at ca. 105°-130° C./0.1 mmHg

Sources & evidence

ORD record
ord-90cfccae8afa42deb36bdfc45ab2ebdc
Source dataset
uspto-grants-1989_08
Patent number
US04853472

Reaction notes

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