Triethylamine → HCID 21924534, compound

HRID 1793286Notes

Reaction equation

HRID 1793286 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].C=[CH:10][CH2:11][CH:12]([OH:16])[CH2:13][CH:14]=[CH2:15].[CH2:17](N(CC)CC)C>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:16][CH:12]([CH:11]=[CH2:10])[CH2:13][CH2:14][CH:15]=[CH2:17])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17902Hepta-1,6-dien-4-olHCID 5211735-Bromovaleryl chloride

Product 1

HCID 21924534HCID 21924534, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromopentanoyl chloride (3.0 g, 0.015 mol) was added dropwise to 1,6-heptadien-4-ol (1.5 g, 0.013 mol) and triethylamine (1.4 g, 0.014 mol) in DCM (25 cm3). The mixture was stirred for 2 h and washed with dilute hydrochloric acid (20%, 50 cm3), saturated aqueous potassium carbonate solution (50 cm3), water (50 cm3) then dried (MgSO4) and concentrated to a brown oil. The product was purified by dry flash chromatography [silica gel, DCM] to yield a pale yellow oil (1.7 g, yield 48%). Purity >92% (GC).

Workup

  1. washwashed with dilute hydrochloric acid (20%, 50 cm3), saturated aqueous potassium carbonate solution (50 cm3), water (50 cm3)
  2. dry with materialthen dried (MgSO4)
  3. concentrationconcentrated to a brown oil
  4. customThe product was purified
  5. dry with materialby dry flash chromatography [silica gel, DCM]

Sources & evidence

ORD record
ord-47f59773229d4319a93d7c9cf0becb3a
Source dataset
uspto-grants-2006_07
Patent number
US07081307B2

Reaction notes

Loading…