Hydrochloric Acid → HCID 88313714, compound

HRID 1497013Notes

Reaction equation

HRID 1497013 reaction equation
[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[C:13](OCC)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C.Cl>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14487Diisobutylaluminum hydrideHCID 20628704HCID 20628704, compound

Product 1

HCID 88313714HCID 88313714, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl (2E,4E)-7-phenylhepta-2,4-dienoate (7.32 g) in dry toluene (75 ml) was cooled to −78° C. DIBAL-H (1M in hexanes, 65.2 ml) was added dropwise and the mixture was stirred for 3 h. The mixture was allowed to warm-up to room temperature and hydrolyzed with 1M aqueous HCl with cooling in ice/water bath. Additional, 3M aqueous HCl was added until pH=1. The layers were separated and the aqueous layer was extracted three times with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography to yield a colorless oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted three times with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. customto yield a colorless oil

Sources & evidence

ORD record
ord-924590a64a404d1cacb37b6db68e7cb0
Source dataset
uspto-grants-2015_12
Patent number
US09199948B2

Reaction notes

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