Potassium Carbonate → HCID 19041757, compound

HRID 1684055Notes

Reaction equation

HRID 1684055 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](OS(C)(=O)=O)[CH:8]=[CH2:9].[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([CH:24]3[CH:30]([CH3:31])[C:29]45[CH2:38][CH:26]([O:27][C:28]4=[CH:35][C:34](=[O:36])[C:33]([OH:37])=[CH:32]5)[CH2:25]3)=[CH:23][C:18]=2[O:17][CH2:16]1>CN(C=O)C.C(Cl)Cl>[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([CH:24]3[CH:30]([CH3:31])[C:29]45[CH2:38][CH:26]([O:27][C:28]4=[CH:35][C:34](=[O:36])[C:33]([OH:37])=[C:32]5[CH2:9][CH:8]=[CH2:7])[CH2:25]3)=[CH:23][C:18]=2[O:17][CH2:16]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81214Allyl methanesulfonate2×HCID 19041752HCID 19041752, compound

Product 1

HCID 19041757HCID 19041757, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Potassium carbonate (172.7 mg, 1.25 mmol) and mesyl allyl ether (113 mg, 0.83 mmol) are added to a stirred solution of 4-(1,3-benzodioxol-5-yl)-2,3,4,5-tetrahydro-7-hydroxy-5-methyl-8H-2,5a-methano-1-benzoxepin-8-one (109, as prepared in Example 54) in DMF (4 ml). The reaction is stirred at room temperature overnight, after which time TLC still shows unreacted starting material present. An additional 50 μl mesyl allyl ether is then added to the reaction and the reaction is then starred for another 24 hours. The reaction is diluted with methylene chloride and washed with 10% HCl followed by water. The extract is dried over sodium sulfate and concentrated in vacuo. The reaction is best purified by medium pressure liquid chromatography (MPLC) (i.e., flash chromatography on silica gel (25 g, 1:1 hexane-ethyl acetate as eluant) produces a contaminated product as determined by 1H NMR and flash chromatography on silica gel (30 g silica, 1:1:1 hexane-ethyl ether-methylene chloride) also produces a contaminated product as determined by 1H NMR). M+(CI)=367. 1H NMR: 0.64 (3H, d), 1.67 (1H, dd), 1.89 (1H, d), 2.06 (1H, m), 2.26 (2H, m), 2.49 (3H, m), 2.72 (1H, dd), 3.05 (1H, t), 5.08 (3H, m), 5.92 (2H, s), 6.15 (1H, s), 6.65 (3H, m).

Workup

  1. waitthe reaction is then starred for another 24 hours
  2. washwashed with 10% HCl
  3. dry with materialThe extract is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe reaction is best purified by medium pressure liquid chromatography (MPLC) (i.e., flash chromatography on silica gel (25 g, 1:1 hexane-ethyl acetate as eluant)
  6. customproduces a contaminated product
  7. customalso produces a contaminated product

Sources & evidence

ORD record
ord-eb6190cfcc4e48e9a13ebdff6703a205
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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