Dichloromethane → HCID 57672411, compound

HRID 2101794Notes

Reaction equation

HRID 2101794 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9](/[CH:16]=[CH:17]/[CH3:18])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([CH3:19])[CH:4]=1.C(Cl)Cl.B(Br)(Br)Br>>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9](/[CH:16]=[CH:17]/[CH3:18])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([CH3:19])[CH:4]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 57672468HCID 57672468, compound

Product 1

HCID 57672411HCID 57672411, compoundYield 25%

Procedure

To a stirred solution of (S,E)-ethyl 3-(4-methoxy-2-methylphenyl)hex-4-enoate 28.6 (0.500 g, 2 mmol) in DCM (19 mL, 2 mmol) at 0° C. was added boron tribromide (9 mL, 9 mmol). The resulting mixture was stirred for 1 hour. The reaction wasquenched by the addition of pH 7 buffer. The resulting mixture was extracted with DCM. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford (S,E)-ethyl 3-(4-hydroxy-2-methylphenyl)hex-4-enoate (28.7) (0.12 g, 25% yield) as a colorless oil. MS ESI (pos.) m/e: 266.2 (M+H2O), 249.1 (M+H).

Workup

  1. additionThe reaction wasquenched by the addition of pH 7 buffer
  2. extractionThe resulting mixture was extracted with DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-aec3c867b5eb4d3db8e74678bbf49242
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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