Dimethyl Sulfoxide → HCID 53736439, compound

HRID 1637119Notes

Reaction equation

HRID 1637119 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]1([O:16][C:17]2[CH:18]=[C:19]([CH:25]([C:29]#[C:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:26][CH2:27][OH:28])[CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(N(CC)CC)C.[NH4+].[Cl-]>C(Cl)Cl>[CH:11]1([O:16][C:17]2[CH:18]=[C:19]([CH:25]([C:29]#[C:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:26][CH:27]=[O:28])[CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 54396505HCID 54396505, compound

Product 1

HCID 53736439HCID 53736439, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (0.265 mL, 3.0 mmol) in CH2Cl2 (11 mL) at -78° C. under an argon atmosphere was added DMSO (0.43 mL, 6.0 mmol). After 0.03 h, (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-phenylpent4ynol (0.96 g, 2.74 mmol) was added in CH2Cl2 (15 mL). After 0.25 h, triethylamine (2.0 mL, 13.7 mmol) was added. The mixture was allowed to warm to room temperature. Aqueous NH4Cl was added, the mixture was extracted three times with CH2Cl2, the organic extract was washed with 1N HCl, was dried (Na2SO4) and was evaporated. Purification by flash chromatography (silica gel, 25% EtOAc/Hex) provided the title compound as a yellow oil (0.59 g, 62%).MS(EI) m/e 349 [M+H]+.

Workup

  1. waitAfter 0.25 h
  2. extractionthe mixture was extracted three times with CH2Cl2
  3. extractionthe organic extract
  4. washwas washed with 1N HCl
  5. dry with materialwas dried (Na2SO4)
  6. customwas evaporated
  7. customPurification by flash chromatography (silica gel, 25% EtOAc/Hex)

Sources & evidence

ORD record
ord-7eef4a7fbed2441692df03c170734a8b
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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