Diethyl Ether → 1-(3-(((2-Tetrahydropyranyl)oxy)methyl)phenyl)-2-propen-1-ol

HRID 2259490Notes

Reaction equation

HRID 2259490 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13].[CH:17]([Mg]Br)=[CH2:18].CCOCC>C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:12]([OH:13])[CH:17]=[CH2:18])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 190029373-(((2-Tetrahydropyranyl)oxy)methyl)benzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 190029401-(3-(((2-Tetrahydropyranyl)oxy)methyl)phenyl)-2-propen-1-olYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To the aldehyde of Step 10 (85 g, 386 mmol) in toluene (1 L) at 0° C. was slowly added vinyl magnesium bromide in Et2O (450 mL, 1M, 450 mmol) over a 30 minute period. After stirring for 1 hr at 0° C., the reaction mixture was quenched with 25% aq. NH4OAc and extracted with EtOAc (3×). Evaporation and purification by flash chromatography (15%→25% EtOAc in toluene) yielded 82 g (86%) of the title compound.

Workup

  1. customat 0° C.
  2. customover a 30 minute
  3. customthe reaction mixture was quenched with 25% aq. NH4OAc
  4. extractionextracted with EtOAc (3×)
  5. customEvaporation and purification by flash chromatography (15%→25% EtOAc in toluene)

Sources & evidence

ORD record
ord-d2a1e56511c4427a8e843b039a85019e
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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