Tetrahydrofuran → HCID 22613112, compound

HRID 844366Notes

Reaction equation

HRID 844366 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:15][CH3:16])[C:9]=1[O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[O:6].C1COCC1.[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[OH:6])[CH:7]=[C:8]([O:15][CH3:16])[C:9]=1[O:10][CH2:11][CH2:12][O:13][CH3:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 13188736HCID 13188736, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 22613112HCID 22613112, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a 1l round bottomed flask with a stirring bar and an argon inlet was added 3-bromo-4-(2-methoxyethoxy)-5-methoxybenzaldehyde (12.00 g, 41.50 mmol) and dry THF (150 mL). This solution was cooled in an ice bath and phenylmagnesiumbromide in diethyl ether (16.6 mL of a 3.0 M solution, 49.81 mmol) was added with a syringe. The resulting solution was stirred for 1 h at 0° C. The reaction was quenched with aqueous NH4Cl solution. The mixture was diluted with EtOAc and the layers were separated. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. This material was chromatographed on 400g of silica gel using 30/70 EtOAc-hexane as eluant. There was obtained 1-(3-bromo-4-(2-methoxyethoxy)-5-methoxyphenyl)-1-phenylmethanol as an oil. 1H NMR (CDCl3): δ2.29 (d, j=4Hz, 1H); 3.44 (s, 3H); 3.74 (t, j=4 Hz, 2H); 3.82 (s, 3H); 4.13 (t, j=4 Hz, 2H); 5.75 (d, j=4Hz, 1H); 6.88 (s, 1H); 7.12 (s, 1H); 7.35 (m, 5H).

Workup

  1. temperatureThis solution was cooled in an ice bath
  2. customThe reaction was quenched with aqueous NH4Cl solution
  3. additionThe mixture was diluted with EtOAc
  4. customthe layers were separated
  5. washThe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThis material was chromatographed on 400g of silica gel using 30/70 EtOAc-hexane as eluant

Sources & evidence

ORD record
ord-2acc9a0804ea4d2cb4274b7963404819
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

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