(Phenylmethoxy)acetaldehyde → 1-(Benzyloxy)pent-4-en-2-ol

HRID 570294Notes

Reaction equation

HRID 570294 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([Mg]Cl)[CH:13]=[CH2:14]>C1COCC1>[CH2:1]([O:8][CH2:9][CH:10]([OH:11])[CH2:14][CH:13]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 108989(Phenylmethoxy)acetaldehydeHCID 178418473HCID 178418473, compound

Product 1

HCID 100354781-(Benzyloxy)pent-4-en-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(Benzyloxy)acetaldehyde (5 g, 33.3 mmol) in dry THF (10 mL) was added dropwise to a stirred and cooled solution of allylmagnesium chloride (25 mL, 2 M in THF, 50 mmol) in THF (100 mL) at −78° C. After the addition, the solution was allowed to warm to 0° C. and quenched with saturated NH4Cl solution. After standard aqueous work up, the residue was purified over silica using EtOAc and hexane to give 1-(benzyloxy)pent-4-en-2-ol (11).

Workup

  1. additionAfter the addition
  2. customquenched with saturated NH4Cl solution
  3. customAfter standard aqueous work up, the residue was purified over silica

Sources & evidence

ORD record
ord-2ecd7da9568442ffabf69095bebf3b14
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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