Methanol → HCID 86673381, compound

HRID 1023343Notes

Reaction equation

HRID 1023343 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13](OCC)=[O:14])=[CH:7][CH:6]=1)[CH3:2].CC(C[AlH]CC(C)C)C.CO.O>C1(C)C=CC=CC=1>[CH2:19]([O:18][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH2:13][OH:14])=[CH:7][CH:6]=1)[CH3:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 21989703HCID 21989703, compound

Product 1

HCID 86673381HCID 86673381, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of (E)-ethyl 3-(4-(diethoxymethyl)phenyl)acrylate (1.400 g) in toluene (10 mL) was added DIBAH (1 M solution in toluene) (10 mL) at −20° C. under an Ar atmosphere. The mixture was stirred at −20° C. for 1 hour. To the mixture was added MeOH, and then the mixture was heated to room temperature. To the mixture was added water, and the mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1) to afford (E)-3-[4-(diethoxymethyl)phenyl]prop-2-en-1-ol (1.120 g) as a colorless oil.

Workup

  1. temperaturethe mixture was heated to room temperature
  2. extractionthe mixture was extracted with AcOEt
  3. washThe organic layer was washed with saturated aqueous NaCl
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1)

Sources & evidence

ORD record
ord-f0cb617da1ac438fa00b2a7576ef0c96
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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