Hydrochloric Acid → HCID 11694086, compound

HRID 876194Notes

Reaction equation

HRID 876194 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].II.C([O:12][CH3:13])=O.Cl>C1COCC1>[CH2:7]=[CH:6][CH2:5][CH2:4][CH2:3][CH2:2][CH:13]([OH:12])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 7865Methyl formateHCID 759066-Bromo-1-hexene

Product 1

HCID 11694086HCID 11694086, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirring bar and Mg (1.2 g) were placed in a 500 ml-capacity three neck flask, and the flask was connected to a condenser and sufficiently dried. Then, a nitrogen atmosphere was established in the flask, and THF (20 ml) and I2 were added thereto. 1-bromo-5-hexene (7) (8 g, 5 mmol) and THF (10 ml) were added to the brown suspension thus obtained to start a reaction, and heat developed when a color of I2 disappeared. Immediately after the start of the heat development, the flask was placed in an ice bath. Then, after generation of a Grignard reagent, HCOOMe (1.5 ml, 5 mmol) was slowly dropped into the flask, and the mixture thus obtained was stirred for 30 minutes. When generation of alcohol was recognized by thin-layer chromatography, diluted hydrochloric acid was added to the mixture to stop the reaction. An organic layer was extracted with AcOEt and dried over Na2SO4, and the solvent was distilled off under reduced pressure. Thereafter, the organic layer was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1), (hexane:ethyl acetate=4:1). Thus, intended 1,12-tridecadiene-7-ol (8) (2.55 g, 1.3 mmol, yield: 26%) was obtained. 1HNMR values of 1,12-tridecadiene-7-ol (8) are shown below.

Workup

  1. customthe flask was connected to a condenser
  2. customsufficiently dried
  3. additionwere added
  4. customthus obtained
  5. customa reaction
  6. temperatureheat
  7. customImmediately after the start of the heat development, the flask was placed in an ice bath
  8. customthe mixture thus obtained
  9. additionwas added to the mixture
  10. customthe reaction
  11. extractionAn organic layer was extracted with AcOEt
  12. dry with materialdried over Na2SO4
  13. distillationthe solvent was distilled off under reduced pressure
  14. customThereafter, the organic layer was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1), (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-f6f43a22bdd74dc9855d86d19f563c8b
Source dataset
uspto-grants-2015_03
Patent number
US08987044B2

Reaction notes

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