Dimethyl Sulfoxide → HCID 59678324, compound

HRID 1392664Notes

Reaction equation

HRID 1392664 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH3:20])[C:14]=1[C:21]1[N:26]=[C:25]([CH3:27])[C:24]([CH:28]([CH:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][CH2:32][CH2:31]2)[OH:29])=[C:23]([O:40][CH3:41])[CH:22]=1)[CH3:12].C(N(CC)CC)C>ClCCl>[CH2:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:11][CH3:12])[C:14]=1[C:21]1[N:26]=[C:25]([CH3:27])[C:24]([C:28]([CH:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][CH2:32][CH2:31]2)=[O:29])=[C:23]([O:40][CH3:41])[CH:22]=1)[CH3:20]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66993663HCID 66993663, compound

Product 1

HCID 59678324HCID 59678324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dimethyl sulfoxide (60 μL, 0.85 mmol) is added at −78° C. to a solution of oxalyl chloride (36 μL, 0.41 mmol) in dichloromethane (2 mL). After stirring at −78° C. for 10 minutes, a solution of [6-(2,6-diethyl-phenyl)-4-methoxy-2-methyl-pyridin-3-yl]-(1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol (138 mg) in dichloromethane (2 mL) is added and the mixture is stirred for 40 minutes more. Triethylamine (0.24 mL, 1.7 mmol) is then added. After 10 minutes, the mixture is allowed to warm to room temperature and quenched with water. Extraction with dichloromethane, drying (Na2SO4), and concentration followed by flash chromatography provides [6-(2,6-diethylphenyl)-4-methoxy-2-methylpyridin-3-yl]-(1,2,3,4-tetrahydronaphthalene-1-yl)methanone. 1H NMR (CDCl3) 7.30 (dd, 1H), 7.16-7.12 (m, 4H), 7.0 (t, 1H), 6.9 (d, 1H), 6.6 (s, 1H), 4.4 (s, 1H), 3.8 (s, 3H), 2.90-2.76 (m, 2H), 2.43-2.33 (m, 4H), 2.3 (s, 3H), 2.03-1.84 (m, 4H), 1.15-1.04 (m, 6H).

Workup

  1. stirringthe mixture is stirred for 40 minutes more
  2. waitAfter 10 minutes
  3. temperatureto warm to room temperature
  4. customquenched with water
  5. extractionExtraction with dichloromethane
  6. customdrying
  7. concentration(Na2SO4), and concentration

Sources & evidence

ORD record
ord-4fbf3c5994dd466ba75deba66ed5be0d
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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