Dimethyl Sulfoxide → HCID 18348548, compound

HRID 2268500Notes

Reaction equation

HRID 2268500 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[C:19]([O:26][CH3:27])=[C:18]2[C:14]=1[CH2:15][C:16]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][OH:42])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:17]2.C(N(CC)CC)C>C1COCC1.O>[CH3:27][O:26][C:19]1[C:20]([O:24][CH3:25])=[C:21]([O:22][CH3:23])[C:13]([O:12][CH3:11])=[C:14]2[C:18]=1[CH2:17][C:16]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[O:42])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:15]2

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18348532HCID 18348532, compound

Product 1

HCID 18348548HCID 18348548, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of oxalyl chloride (0.394 ml) in THF (36 ml) was dropwise added a solution of dimethylsulfoxide (468 mg) in THF (2.4 ml) at −70° C. or under nitrogen atmosphere. After the reaction mixture was stirred for 10 min, a solution of 8-(4,5,6,7-tetramethoxy-2-phenylindan-2-yl)octanol (1.00 g) in THF (12 ml) was dropwise added to the reaction mixture at −70° C. or under. After being stirred for 15 min, the reaction mixture was stirred at between −60° C. and −50° C. for 1 hr, to which triethylamine (2.30 ml) was dropwise added. The reaction mixture was allowed to warm to 0° C. and stirred for 20 min, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=4:1) to yield the entitled compound (985 mg) as an oil.

Workup

  1. stirringAfter being stirred for 15 min
  2. additionwas dropwise added
  3. stirringstirred for 20 min
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated aqueous sodium chloride
  6. customdried
  7. customThe solvent was removed in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-790c688c75a1436886379cf10d82dad4
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…