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

HRID 2188039Notes

Reaction equation

HRID 2188039 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 9; 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. Di-chloromethane (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-682c057cc02f4ef1b9e6b7e3aa0d3ba0
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

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