Hydrochloric Acid → HCID 22246935, compound

HRID 2117607Notes

Reaction equation

HRID 2117607 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=[O:6].[CH:11]([Mg]Br)=[CH2:12].Cl.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH:11]=[CH2:12])[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 357463,5-DichlorobenzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 22246935HCID 22246935, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,5-dichlorobenzaldehyde (7.5 g, 43 mmol) in THF (75 mL) was cooled to 0° C. and vinylmagnesium bromide (1M in THF, 48 mL, 48 mmol) was added dropwise. The reaction was warmed to room temperature and was stirred for 16 h. Aqueous HCl (1N) and EtOAc were added. The aqueous solution was washed with EtOAc and the organic solution was dried (MgSO4), filtered, and concentrated. The residue was used in the next step without further purification.

Workup

  1. washThe aqueous solution was washed with EtOAc
  2. dry with materialthe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was used in the next step without further purification

Sources & evidence

ORD record
ord-6d04838d34554a0bb6348e7857198c32
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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