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

HRID 529254Notes

Reaction equation

HRID 529254 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-18719b2491fb4a5a9eed095833ef4768
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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