Dimethyl Sulfoxide → HCID 18177852, compound

HRID 394916Notes

Reaction equation

HRID 394916 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1([CH3:32])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16]([CH:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:25][OH:26])[CH:15]=[CH:14][C:13]1=2.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]1([CH3:32])[CH2:21][CH2:20][C:19]([CH3:22])([CH3:23])[C:18]2[CH:17]=[C:16]([CH:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:25]=[O:26])[CH:15]=[CH:14][C:13]1=2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 17949402HCID 17949402, compound

Product 1

HCID 18177852HCID 18177852, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 0.35 ml of oxalyl chloride in 20 ml of methylene chloride was treated, at −78° C., with 0.4 ml of DMSO absolute. The mixture was stirred at −78° C. for 5 minutes then 554 mg of (RS)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-heptanol dissolved in 4 ml of methylene chloride were added dropwise. The reaction mixture was stirred at −78° C. for 15 minutes. 1.3 ml of triethylamine were added and the mixture was stirred 15 minutes at −78° C. then 2.5 hours at room temperature. The mixture was quenched with 20 ml water and extracted with 3 portions of 20 ml of methylene chloride. The combined extracts were washed with 2 portions of 5 ml of water and 1 portion of 50 ml of a saturated aqueous solution of NaCl. The organic phase was dried over MgSO4 and the solvent evaporated to yield a yellow oil. The product was purified with flash chromatography (SiO2, 5% ethyl acetate/hexanes), to yield 483 mg of a colorless oil, 1H NMR (CDCl3): 9.64 (d, J=2.0 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.08 (d, J=3.0 Hz, 1H), 6.95 (dd, J=8.4, 3.0 Hz, 1H), 3.43 (td, J=7.2, 2.0 Hz, 1H), 2.05 (m, 1H), 1.70 (m, 1H), 1.68 (s, 4H), 1.22-1.40 (m, 6H), 1.27 (s, 12H), 0.86 (m, 3H).

Workup

  1. additionwere added dropwise
  2. stirringThe reaction mixture was stirred at −78° C. for 15 minutes
  3. stirringthe mixture was stirred 15 minutes at −78° C.
  4. custom2.5 hours
  5. customat room temperature
  6. customThe mixture was quenched with 20 ml water
  7. extractionextracted with 3 portions of 20 ml of methylene chloride
  8. washThe combined extracts were washed with 2 portions of 5 ml of water and 1 portion of 50 ml of a saturated aqueous solution of NaCl
  9. dry with materialThe organic phase was dried over MgSO4
  10. customthe solvent evaporated
  11. customto yield a yellow oil
  12. customThe product was purified with flash chromatography (SiO2, 5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-200cf24bdd52471c835e6202681e30ec
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

Loading…