Dimethyl Sulfoxide → HCID 86702733, compound

HRID 511743Notes

Reaction equation

HRID 511743 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C:19]1[CH:26]2[CH:22]([CH2:23][CH:24]([CH2:27][OH:28])[CH2:25]2)[C:21](=[O:29])[C:20]=1[C:30]1[C:35]([CH2:36][CH3:37])=[CH:34][C:33]([CH3:38])=[CH:32][C:31]=1[CH2:39][CH3:40])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[CH2:11]([O:18][C:19]1[CH:26]2[CH:22]([CH2:23][CH:24]([CH:27]=[O:28])[CH2:25]2)[C:21](=[O:29])[C:20]=1[C:30]1[C:35]([CH2:36][CH3:37])=[CH:34][C:33]([CH3:38])=[CH:32][C:31]=1[CH2:39][CH3:40])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 67512328HCID 67512328, compound

Product 1

HCID 86702733HCID 86702733, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At −78° C., 1.31 g (16.8 mmol) of dimethyl sulphoxide are slowly added dropwise to 1.067 g (8.4 mmol) of oxalyl chloride in 40 ml of dichloromethane, and the mixture is stirred at this temperature for 20 min. 1.70 g (4.20 mmol) of 3-(benzyloxy)-2-(2,6-diethyl-4-methylphenyl)-5-(hydroxymethyl)-4,5,6,6a-tetrahydropentalen-1(3aH)-one (Example I-a-1), dissolved in 30 ml of dichloromethane, are then slowly added dropwise, and the mixture is stirred for another hour. 2.13 g (21 mmol) of triethylamine are then added slowly, and the mixture is brought to room temperature. Addition of 50 ml of saturated ammonium chloride solution, separation, washing of the organic phase with water, drying (magnesium sulphate), concentration on a rotary evaporator and chromatographic purification of the resulting crude product on silica gel (mobile phase ethyl acetate/hexane 1:5) gives 1.24 g (73%) of the title compound as a colourless oil.

Workup

  1. additionare then slowly added dropwise
  2. stirringthe mixture is stirred for another hour
  3. customis brought to room temperature
  4. washwashing of the organic phase with water
  5. customdrying
  6. concentration(magnesium sulphate), concentration
  7. customon a rotary evaporator and chromatographic purification of the resulting crude product on silica gel (mobile phase ethyl acetate/hexane 1:5)

Sources & evidence

ORD record
ord-10eab8c57c194db281e790ccea14a280
Source dataset
uspto-grants-2015_08
Patent number
US09101133B2

Reaction notes

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