Sodium Carbonate → HCID 10690272, compound

HRID 2394504Notes

Reaction equation

HRID 2394504 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)([CH2:9]O)[CH2:5][CH2:4]1.C(N(S(F)(F)[F:33])CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[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)([CH2:9][F:33])[CH2:5][CH2:4]1

Participants

5

Reactant 3

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

Product 1

HCID 10690272HCID 10690272, compoundYield 80.3%

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, 5% aqueous 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-0a88f8e0e45344749163f3798e72850f
Source dataset
uspto-grants-1998_09
Patent number
US05811455

Reaction notes

Loading…