Water → HCID 22014352, compound

HRID 1532868Notes

Reaction equation

HRID 1532868 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10]([Mg]Cl)[CH2:11][CH2:12][CH3:13].O.Cl.CCOCC>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:10][CH2:11][CH2:12][CH3:13])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 114773-ChlorobenzaldehydeHCID 10953452Ether hydrochlorideHCID 178418265HCID 178418265, compound

Product 1

HCID 22014352HCID 22014352, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-chlorobenzaldehyde (1.4 g, 10 mmol) in THF (10 mL) was cooled to −10° C., then 2.0 M n-butylmagnesium chloride (10 mL) was added. The reaction was allowed to warm to RT under N2 overnight. Next day the reaction was cooled to 0−5° C., water (5 mL) was added, followed by 2N HCl—Et2O partition. The organic layer was washed with brine, then dried over Na2SO4. After filtration and concentration the crude material was purified by chromatography using 9/1 hex/EtOAc. Recovered 1.25 g (63%).

Workup

  1. temperatureNext day the reaction was cooled to 0−5° C.
  2. custompartition
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration the crude material
  6. customwas purified by chromatography
  7. customRecovered 1.25 g (63%)

Sources & evidence

ORD record
ord-634d7cb00c594998a95f56e2626e1c32
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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