Dimethyl Sulfoxide → HCID 59305173, compound

HRID 2240137Notes

Reaction equation

HRID 2240137 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6](/[CH:11]=[CH:12]/[C:13]([N:15]2[CH2:20][CH2:19][CH:18]([CH:21]=[O:22])[CH2:17][CH2:16]2)=[O:14])[CH:7]=[C:8]([F:10])[CH:9]=1.[CH3:23]S(C)=O>>[F:10][C:8]1[CH:7]=[C:6](/[CH:11]=[CH:12]/[C:13]([N:15]2[CH2:16][CH2:17][CH:18]([CH:21]3[CH2:23][O:22]3)[CH2:19][CH2:20]2)=[O:14])[CH:5]=[C:4]([F:3])[CH:9]=1

Participants

4

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 59305196HCID 59305196, compound

Product 1

HCID 59305173HCID 59305173, compoundYield 58%

Conditions

Temperature
0 °C

Procedure

An oven dried 500-mL flask was charged with (CH3)3SOI (46.14 g, 210 mmol, 1.3 eq) and 250 mL dry DMSO. NaH (95%, 5.30 g, 210 mmol, 1.3 eq) was added in around 10 batches and solution was then cooled to 0° C. The resulting mixture was stirred at 0° C. for 30 min. The aldehyde (Intermediate 2, 45 g, 161 mmol, 1.0 eq) in 150 mL dry DMSO solution was added dropwise and the resulting solution was stirred at 0° C. for 30 min. LCMS showed completed reaction. The reaction was then quenched with 800 mL water and poured into 1200 mL diethyl ether. The organic layer was separated and washed with 2×150 mL water and dried over MgSO4 and concentrated. Crude LCMS showed >90% purity for the desired product in 58% yield as a light yellow oil which solidified to a yellow solid overnight. MS (ES) m/e 294 [M+H]+. 1HNMR (CDCl3) δ(ppm): 7.56 (d, 1H), 7.04 (dd, 2H), 6.91 (d, 1H), 6.80 (m, 1H), 4.74 (m, 1H), 4.11 (m, 1H), 3.05 (m, 1H), 2.77 (s, 2H), 2.61 (m, 1H), 1.95 (m, 1H), 1.70-1.80 (m, 1H), 1.30-1.60 (m, 4H).

Workup

  1. customAn oven dried 500-mL flask
  2. stirringthe resulting solution was stirred at 0° C. for 30 min
  3. customreaction
  4. customThe reaction was then quenched with 800 mL water
  5. additionpoured into 1200 mL diethyl ether
  6. customThe organic layer was separated
  7. washwashed with 2×150 mL water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customsolidified to a yellow solid overnight

Sources & evidence

ORD record
ord-f39b6d1dda074d1b919231bff26ca095
Source dataset
uspto-grants-2010_05
Patent number
US07723350B2

Reaction notes

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