Water → HCID 10125893, compound

HRID 480974Notes

Reaction equation

HRID 480974 reaction equation
[CH3:1][C:2]1[C:17]([CH3:18])=[C:16]([O:19][CH2:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:15]=[CH:14][C:3]=1[O:4][CH2:5][C:6](C1C=CC=CC=1)=O.BrCC([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=O.O>C1(C)C(C)=CC=CC=1>[CH3:18][C:17]1[C:16]2[O:19][CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]=2[C:14]2[C:6]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:5][O:4][C:3]=2[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 12112128HCID 12112128, compound

Product 1

HCID 10125893HCID 10125893, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2-[2,3-Dimethyl-4-(2-oxo-2-phenyl-ethoxy)-phenoxy]-1-phenyl-ethanone (480 mg, 1.28 mmol) synthesized as described in Example 11, an excess of bromoacetophenone, and polyphosphoric acid (PPA, 100 mg) in xylene (10 mL) was stirred at 150° C. for 10 h. The mixture was then poured into water, extracted with EtOAc, the organic layer was washed with water and brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column eluting with 10-20% EtOAc in hexane to give 190 mg of 4,5-dimethyl-1,8-diphenyl-benzo[1,2-b;4,3-b′]difuran (250 mg). 1H NMR (CDCl3, 300 MHz) δ: 7.60 (s, 2H), 7.05 (m, 4H), 6.90 (m, 2H), 6.85 (m, 4H), 2.60 (s, 6H) ppm. 13C NMR (CDCl3, 75 MHz) δ: 152.57,141.48, 133.19, 128.42, 127.52, 126.87, 124.05, 117.40, 116.29, 11.80 ppm. MS (m/z): 339 (M+H+).

Workup

  1. customsynthesized
  2. extractionextracted with EtOAc
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column
  7. washeluting with 10-20% EtOAc in hexane

Sources & evidence

ORD record
ord-c0359d3f324a44bab7d9b89b18b5cd26
Source dataset
uspto-grants-2003_11
Patent number
US06653346B1

Reaction notes

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