Tetrahydrofuran → HCID 18615581, compound

HRID 1265338Notes

Reaction equation

HRID 1265338 reaction equation
O1CCC[CH2:2]1.[Br:6][C:7]1[CH:8]=[C:9]([CH:16]=[O:17])[C:10]2[O:14][CH2:13][O:12][C:11]=2[CH:15]=1.C[Mg]Br>C(OCCCC)CCC>[Br:6][C:7]1[CH:8]=[C:9]([CH:16]([OH:17])[CH3:2])[C:10]2[O:14][CH2:13][O:12][C:11]=2[CH:15]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 125140976-Bromo-2H-1,3-benzodioxole-4-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 18615581HCID 18615581, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Conditions

Temperature
25 °C

Procedure

To 150 mL tetrahydrofuran, was added 6-bromo-benzo[1,3]dioxole-4-carbaldehyde (15 g, 65.4 mmol). To the solution was added a solution of methyl magnesium bromide (1.0 M) in di-n butyl ether (72 mL) followed by exotherm and solid formation. The mixture was stirred at 25° C. for 2.5 hours and evaporated in vacuo to a solid. The mixture was suspended in ethyl acetate washed with 1N citric acid, brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and evaporated to an oil. The oil was induced to crystallize from ethyl acetate and hexane giving a white solid which was filtered and dried in vacuo giving a solid, 10.48 g, 65.4% yield. NMR spectra and elemental analysis were consistent with the structure.

Workup

  1. customevaporated in vacuo to a solid
  2. washwashed with 1N citric acid, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customevaporated to an oil
  6. customto crystallize from ethyl acetate and hexane giving a white solid which
  7. filtrationwas filtered
  8. customdried in vacuo
  9. customgiving a solid, 10.48 g, 65.4% yield

Sources & evidence

ORD record
ord-fad1946a886f4033b06208a409ac4149
Source dataset
uspto-grants-2003_04
Patent number
US06545150B2

Reaction notes

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