Hydrochloric Acid → HCID 69435025, compound

HRID 1297036Notes

Reaction equation

HRID 1297036 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+].Cl>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 17825616HCID 17825616, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 69435025HCID 69435025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 8-benzyloxyoctanoate was dissolved in 15 ml of THF. 15 ml (30 mmol) of phenylmagnesium bromide (2 M THF solution) was added dropwise to the obtained solution in ice bath. After stirring at room temperature for 4 hours, a saturated aqueous ammonium chloride solution and then 1 N hydrochloric acid were added to the reaction mixture to terminate the reaction. After the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under educed pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1) to obtain the title compound.

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionAfter the extraction with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under educed pressure
  6. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-82d0fd13484540769c564af6b2765f83
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

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