Sodium Carbonate → HCID 56607736, compound

HRID 2399423Notes

Reaction equation

HRID 2399423 reaction equation
[CH3:1][O:2][C:3]1([O:25][CH3:26])[CH2:8][CH2:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)(CO)[CH2:5][CH2:4]1.C(N(S(F)(F)[F:33])CC)C.[C:36](=[O:39])([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:26][O:25][C:3]1([O:2][CH3:1])[CH2:4][CH2:5][C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:12]=2)([O:39][CH2:36][F:33])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 10594951HCID 10594951, compound

Product 1

HCID 56607736HCID 56607736, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(hydroxymethyl)cyclohexan-1-one dimethyl ketal (0.37 g, 1.02 mmol) in methylene chloride (5 mL) was added dropwise to a solution of diethylaminosulfur trifluoride (0.14 mL, 1.02 mmol) at -78° C. under an argon atmosphere. The mixture was allowed to warm to room temperature and after 0.75 h, 5aqueous sodium carbonate was added. The mixture was extracted with chloroform, the organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo to provide a yellow oil (0.3 g, 80%).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. extractionthe organic extract
  3. dry with materialwas dried (magnesium sulfate)
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d4f3776386a74bd2a3d1078347835eaa
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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