Dimethyl Sulfoxide → HCID 58026141, compound

HRID 2387318Notes

Reaction equation

HRID 2387318 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][C@@:10]([C:15]([F:18])([F:17])[F:16])([OH:14])[CH2:11][C:12]#[CH:13])=[C:4]([CH2:21][OH:22])[CH:3]=1.CS(C)=O.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][C@:10]([OH:14])([C:15]([F:17])([F:18])[F:16])[CH2:11][C:12]#[CH:13])=[C:4]([CH:3]=1)[CH:21]=[O:22]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 58026144HCID 58026144, compound

Product 1

HCID 58026141HCID 58026141, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 15 g (0.040 mol) of (S)-6-(4-fluoro-2-hydroxymethylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol in 150 mL DCM at 0° C. was added 21.3 mL of DMSO and 21.2 mL of triethylamine. The reaction was cooled to 0° C. then 19.1 g (0.12 mol) of Pyr-SO3 was added. The reaction mixture was stirred at 0° C. for 1 hour. The reaction was then quenched with 500 mL of water, acidified with 1 N HCl to pH=2, and the organic layer was separated. The aqueous phases were then extracted with DCM. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 5-fluoro-2-((S)-3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzaldehyde as a thick yellow oil.

Workup

  1. addition19.1 g (0.12 mol) of Pyr-SO3 was added
  2. customThe reaction was then quenched with 500 mL of water
  3. customthe organic layer was separated
  4. extractionThe aqueous phases were then extracted with DCM
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ae7f86a6a1d492d8f3497a47308a578
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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