Methanol → HCID 54260281, compound

HRID 1646228Notes

Reaction equation

HRID 1646228 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:16]=[CH:15][C:8]([CH:9]=[CH:10][C:11](OC)=[O:12])=[CH:7][C:6]=1[N+:17]([O-:19])=[O:18].CO.O>C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:16]=[CH:15][C:8]([CH:9]=[CH:10][CH2:11][OH:12])=[CH:7][C:6]=1[N+:17]([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 54420533HCID 54420533, compound

Product 1

HCID 54260281HCID 54260281, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21225700DiisobutylaluminumhydrideSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under a current of argon, a solution of 710 mg of methyl 4-methoxymethoxy-3-nitrocinnamate in 6 ml of toluene and 4.4 ml of diisobutyl aluminum hydride (1.5M toluene solution) added thereto at -78° C. were stirred for 30 minutes. The produced reaction solution was combined with methanol at -78° C. to effect decomposition of excess diisobutyl aluminum hydride and then the resultant mixture and water added thereto at 0° C. were stirred for a while. Subsequently, the mixture was filtered with sellaite and wased with ethyl acetate and the filtrate was extracted from ethyl acetate. The consequently separated organic layer was washed with saturated saline solution and then with anhydrous sodium sulfate and concentrated under a vacuum. The resultant concentrate was subjected to silica gel column chromatography. From the hexane-ethyl acetate (1:1 V/V) eluate, 560 mg of 4-methoxymethoxy-3-nitrocinnamyl alcohol was obtained in the form of a yellow oily substance. The yield was 88%.

Workup

  1. customThe produced reaction solution
  2. stirringat 0° C. were stirred for a while
  3. filtrationSubsequently, the mixture was filtered with sellaite
  4. extractionthe filtrate was extracted from ethyl acetate
  5. washThe consequently separated organic layer was washed with saturated saline solution
  6. concentrationwith anhydrous sodium sulfate and concentrated under a vacuum
  7. concentrationThe resultant concentrate

Sources & evidence

ORD record
ord-070083ebed704f78911792b5a04f47a0
Source dataset
uspto-grants-1993_01
Patent number
US05179105

Reaction notes

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