Thiophenol → HCID 87106486, compound

HRID 922330Notes

Reaction equation

HRID 922330 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)\[CH2:5][O:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[O:23]C(=O)O[CH:20]3[C:25]([O:27][CH3:28])=[O:26])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[CH2:37](N(CC)CC)C.[C:44]1([SH:50])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1COCC1>[OH:23][CH:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:10]2[CH:29]=[CH:30][C:7]([O:6][CH2:5]/[C:4](=[N:3]\[O:2][CH3:1])/[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:8][CH:9]=2)=[CH:14][CH:15]=1)[CH:20]([S:50][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:25]([O:27][CH2:28][CH3:37])=[O:26]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 87106347HCID 87106347, compound

Product 1

HCID 87106486HCID 87106486, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}-2-oxo-1,3-dioxolane-4-carboxylate (0.8 g, 1.6 mmol) in THF was added Triethylamine (0.32 g, 3.2 mmol) and Thiophenol (0.34 g, 3.2 mmol) at 0° C. under argon then slowly warmed to RT, then stirring continued at 60° C. for 12 h. Reaction mass quenched with water and extracted with ethyl acetate, organic layer was washed with water and brine, dried over sodium sulphate and concentrated to yellow oil which was further purified by column (60-120 silica) using 20% ethyl acetate in pet ether to get the titled compound as yellow oil. (0.55 g, Yield: 61%) 1H NMR (300 MHz, DMSO): δ 7.62-7.65 (m, 2H), 7.27-7.40 (m, 8H), 7.22-7.24 (m, 2H), 7.11-7.14 (m, 2H), 6.90-6.93 (d, 4H), 5.21 (s, 2H), 5.01 (s, 2H), 4.63-4.73 (m, 1H), 4.01 (s, 3H), 3.89-3.91 (d, 1H), 3.59 (s, 3H).

Workup

  1. customReaction mass
  2. customquenched with water
  3. extractionextracted with ethyl acetate, organic layer
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to yellow oil which
  7. customwas further purified by column (60-120 silica)

Sources & evidence

ORD record
ord-b33aaf6fefdf4756955cd39975381819
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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