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

HRID 414142

Reaction equation

HRID 414142 reaction equation
[CH3:1][C@H:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH2:3]/[CH:4]=[CH:5]/[C@H:6]([OH:8])[CH3:7].[C:15]([O-])(=[O:19])[CH2:16]CC.C(OC(=O)C)(=O)C.N1C=CC=CC=1>>[C:15]([O:8][C@@H:6](/[CH:5]=[CH:4]/[CH2:3][C@H:2]([CH3:1])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH3:7])(=[O:19])[CH3:16]

Participants

5

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 104775ButyrateHCID 11116980(2R,3E,6R)-6,10-dimethyl-3,9-undecadien-2-ol

Product 1

HCID 14368739(2R,3E,6R)-6,10-dimethyl-3,9-undecadien-2-ol acetateYield 99%

Procedure

A flame-dried 100 mL, three-necked flask with magnetic stirring bar was charged under argon with 2.0 g (10.2 mmol) of (2R,3E,6R)-6,10-dimethyl-3,9-undecadien-2-ol [(2R,6R)/(2S,6R)=90:10 by GC diastereomer analysis of butyrate derivative]. Then, after cooling in an ice-bath, 1.5 g (1.4 mL, 15 mmol) of acetic anhydride, 1.58 g (1.6 mL, 20 mmol) of dry pyridine and 12.3 mg (0.1 mmol) of 4-N,N-dimethylaminopyridine were added, and the reaction was stirred for 75 minutes at ambient temperature. Work-up as described in Example 9 followed by Kugelrohr distillation at ca. 110°/0.25 mm afforded 2.35 g (99%) of (2R,3E,6R)-6,10-dimethyl-3,9-undecadien-2-ol acetate as colorless liquid; GC purity 90%; [α]D25 =+47.17° (5.3% in CHCl3).

Workup

  1. temperatureThen, after cooling in an ice-bath
  2. distillationfollowed by Kugelrohr distillation at ca. 110°/0.25 mm

Sources & evidence

ORD record
ord-c7c77e79240c409886ff0bef14cb9967
Source dataset
uspto-grants-1988_12
Patent number
US04789750

Linked notes

Loading…