Dichloromethane → 5-(Benzyloxy)pent-3-en-2-one

HRID 1242118Notes

Reaction equation

HRID 1242118 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl[CH2:15]Cl.[O:17]1[CH2:21][CH2:20]CC1>O>[CH2:1]([O:8][CH2:9][CH:10]=[CH:15][C:21](=[O:17])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 108989(Phenylmethoxy)acetaldehyde

Product 1

HCID 695857455-(Benzyloxy)pent-3-en-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzyloxyacetaldehyde (0.90 g; 6.0 mmol) and dimethyl(2-oxomethyl)phosphonate (1.0 g; 6.0 mmol) were dissolved in a mixture of tetrahydrofuran (25 ml) and water (20 ml). 1N Aqueous potassium hydroxide (6 ml) was added and the mixture was stirred for 30 min. Dichloromethane (50 ml) was added and the organic phase was separated, dried (MgSO4) and evaporated in vacuo leaving 5-benzyloxypent-3-en-2-one.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-df13f1f033364f18b7b6c13b5babc794
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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