Sodium methanethiolate → HCID 19348689, compound

HRID 1418213Notes

Reaction equation

HRID 1418213 reaction equation
[CH3:1][S-:2].[Na+].Br[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:11]([O:26][CH3:27])[CH:10]=1.COCCCOC1C=CC(C(CCCCC)CC(O)=O)=C(OC)C=1>CO.C(OCC)(=O)C>[CH3:1][S:2][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:11]([O:26][CH3:27])[CH:10]=1

Participants

6

Reactant 3

HCID 4378561Sodium methanethiolateHCID 19348523HCID 19348523, compoundHCID 19348642HCID 19348642, compound

Product 1

HCID 19348689HCID 19348689, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

200 mg (2.85 mmol) of sodium thiomethoxide were added to a solution of 278 mg (0.69 mmol) of methyl 3-[4-(3-bromopropoxy)-2-methoxyphenyl]-octanoate, which was a synthetic intermediate of the compound of Preparation 50A, in 6 ml of methanol, and the resulting mixture was stirred for 1 hour. The reaction mixture was then diluted with ethyl acetate, and the diluted solution was washed several times with water and once with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 50 g of silica gel, using a 1:3 by volume mixture of ethyl acetate and hexane as the eluent, to give methyl 3-[4-(3-methylthiopropoxy)-2-methoxyphenyl]octanoate containing a small amount of impurities. Oxidation of the product and subsequent treatment of the reaction mixture were conducted in a similar manner to that described in Example 21 to give 230 mg of the sulfone derivative as an oily substance in a 83% yield over the two steps. This product was hydrolyzed in a similar manner to that described in Preparation 7 to give the title compound as an oily substance.

Workup

  1. washthe diluted solution was washed several times with water
  2. dry with materialonce with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate
  3. customThe solvent was then removed by distillation under reduced pressure
  4. customthe resulting residue was purified by column chromatography through 50 g of silica gel
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-7130ce7b0eab4cb5a39bee0637e0fde7
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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