Dimethyl Sulfoxide → HCID 131728082, compound

HRID 645452Notes

Reaction equation

HRID 645452 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([SiH2:15][O:16][C:17]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:18]1[CH2:22][CH2:21][C:20]([CH2:24][OH:25])([CH3:23])[C:19]1([CH3:27])[CH3:26])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.O>[C:11]([SiH2:15][O:16][C:17]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:18]1[CH2:22][CH2:21][C:20]([CH3:23])([CH:24]=[O:25])[C:19]1([CH3:27])[CH3:26])([CH3:12])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 131728083HCID 131728083, compound

Product 1

HCID 131728082HCID 131728082, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (0.977 mL, 11.2 mmol) in dry CH2Cl2 (20 mL) at −78° C. was added dropwise DMSO (1.19 mL, 16.8 mmol) in dry CH2Cl2 (2.0 mL) over a period of 10 minutes and the mixture was stirred at −78° C. for 15 minutes. A solution of [3-(tert-butyl-diphenyl-silanyloxymethyl)-1,2,2-trimethyl-cyclopentyl]-methanol (2) (2.30 g, 5.6 mmol) in dry CH2Cl2 (6.0 mL) was added dropwise at −78° C. over a period of 30 minutes and the reaction mixture was stirred at −78° C. for 30 minutes. Triethylamine (3.9 mL, 28.0 mmol) was added dropwise at −78° C. over a period of 10 minutes and the reaction mixture was stirred at −78° C. for 1 hour. The temperature of the mixture is allowed to rise to −10° C. over a period of 3.5 hours and cold H2O (60 mL) was added. The organic layer was separated, the aqueous layer was extracted with Et2O (3×60 mL) and the combined organic layers were dried over anhydrous MgSO4. The solvents were removed in vacuo and the residue was purified over silica (n-hexane/ ethyl acetate, 98:2) to afford 2.21 g (97% yield) of the desired product (4) as a viscous oil which was characterized as follows:

Workup

  1. stirringthe reaction mixture was stirred at −78° C. for 30 minutes
  2. stirringthe reaction mixture was stirred at −78° C. for 1 hour
  3. waitto rise to −10° C. over a period of 3.5 hours
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with Et2O (3×60 mL)
  6. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  7. customThe solvents were removed in vacuo
  8. customthe residue was purified over silica (n-hexane/ ethyl acetate, 98:2)

Sources & evidence

ORD record
ord-779fdfa59e69455db7485993eb9db9d6
Source dataset
uspto-grants-2010_04
Patent number
US07704986B2

Reaction notes

Loading…