Water → HCID 70200005, compound

HRID 342432Notes

Reaction equation

HRID 342432 reaction equation
[C:1]([C:4]1[C:5]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[C:6]=2[O:7][C:8]=1[CH3:9])(=[O:3])[CH3:2].[CH3:18][Mg]Br.[Cl-].[NH4+].O>O1CCCC1.C(OCC)C>[C:15]([NH:14][C:10]1[C:6]2[O:7][C:8]([CH3:9])=[C:4]([C:1]([OH:3])([CH3:18])[CH3:2])[C:5]=2[CH:13]=[CH:12][CH:11]=1)(=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 70198796HCID 70198796, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 70200005HCID 70200005, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-acetyl-7-acetylamino-2-methylbenzo[b]furan (2.92 g) in tetrahydrofuran (60 ml) was added a 3M solution of methylmagnesium bromide in diethyl ether (12.7 ml) dropwise with ice cooling. The solution was stirred at ambient temperat ure for 5 hours and to the solution was added aqueous saturated ammonium chloride. Then, the mixture was poured into water and the separated oil was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from methanol to give 7-acetylamino-3-(1-hydroxy-1-methylethyl)-2-methylbenzo[b]furan (1.82 g).

Workup

  1. extractionthe separated oil was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel
  6. customthe obtained oil was crystallized from methanol

Sources & evidence

ORD record
ord-5580fe2f957a453683a1640d4560fd9e
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

Loading…