Triethylamine → Dibenzyl 6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzofuran-7-yl phosphate

HRID 1192000Notes

Reaction equation

HRID 1192000 reaction equation
[OH:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])=[C:7]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[O:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:26][CH3:27].C(Br)(Br)(Br)Br.[CH2:33]([O:40][P:41]([O-:50])[O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[P:41]([O:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])=[C:7]([C:12](=[O:13])[C:14]3[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:26][CH3:27])([O:40][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:50]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 21904359DibenzylphosphiteHCID 24786555Bnc-105

Product 1

HCID 86637653Dibenzyl 6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzofuran-7-yl phosphateYield 94%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.081 g (0.22 mmol) of (7-hydroxy-6-methoxy-2-methylbenzofuran-3-yl)(3,4,5-trimethoxyphenyl)methanone, 0.086 g (0.261 mmol) of carbon tetrabromide and 0.063 ml (0.283 mmol) of dibenzylphosphite in 2.5 ml of anhydrous acetonitrile 0.046 ml of anhydrous triethylamine was added dropwise at 0° C. under nitrogen atmosphere. The resulting mixture was stirred for 2 h at room temperature, then diluted to 20 ml with ethyl acetate, washed with water brine, dried over anhydrous magnesium sulfate, filtered off and evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (dichloromethane/ethyl acetate, 9:1) to give the title compound as a colorless foam (0.13 g, 94%); 1H NMR (CDCl3) δ 2.42 (s, 3H, Me-2); 3.83 (s, 1H, OMe); 3.93 (s, 3H, OMe); 5.33 (m, 4H, CH2Ph); 6.89 (d, CH aromatic, J=8.7 Hz); 7.21 (dd, 1H, CH aromatic, J=8.72 Hz; J=1.2 Hz); 7.08 (s, 2H, CH aromatic); 7.29-7.43 (m, 10H, CH aromatic).

Workup

  1. additionwas added dropwise at 0° C. under nitrogen atmosphere
  2. washwashed with water brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered off
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was purified by flash column chromatography (dichloromethane/ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-1b193cb02e9346a1b6d5d29c30d81032
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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