Ethyl Thioglycolate → HCID 57890097, compound

HRID 1819971Notes

Reaction equation

HRID 1819971 reaction equation
[O-]CC.[Na+].[SH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:12]([Si:16]([CH3:49])([CH3:48])[O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:29]2[S:33][C:32]([CH2:34]OS(C3C=CC(C)=CC=3)(=O)=O)=[C:31]([CH3:46])[CH:30]=2)([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:20][C:19]=1[CH3:47])([CH3:15])([CH3:14])[CH3:13]>CCO>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][S:5][CH2:34][C:32]1[S:33][C:29]([C:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][Si:16]([C:12]([CH3:13])([CH3:15])[CH3:14])([CH3:49])[CH3:48])=[C:19]([CH3:47])[CH:20]=2)([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:30][C:31]=1[CH3:46])[CH3:11]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 57890216HCID 57890216, compound

Product 1

HCID 57890097HCID 57890097, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2.68 M sodium ethoxide (507 μl, 1.36 mmol) in EtOH (2 ml) is added ethyl 2-mercaptoacetate (149 μl, 1.36 mmol) and stirred at RT for 30 m. The mixture is added a solution of toluene-4-sulfonic acid 5-{1-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-thiophen-2-ylmethyl ester (740 mg, 1.29 mmol) in EtOH (2 ml) is added and refluxed for 15 m. The reaction is concentrated and partitioned between EtOAc (100 ml) and 0.2N HCl (50 ml). The organic layer is washed with water (50 ml), dried (MgSO4), concentrated, and chromatographed (12 g SiO2, 5% EtOAc/Hex) to yield the title compound (180 mg, 27%). 1NMR (400 MHz, CDCl3) δ 7.00 (d, 1H, J=2.2 Hz), 6.92 (dd, 1H, J=8.4, 2.2 Hz), 6.64 (d, 1H, J=8.4 Hz), 6.46 (s, 1H), 4.17 (q, 2H, J=7.2 Hz), 3.92 (s, 2H), 3.14 (s, 2H), 2.16 (s, 3H), 2.12 (s, 3H), 2.07-1.98 (m, 4H), 1.28 (t, 3H, J=7.0 Hz), 1.00 (s, 9H), 0.68 (t, 6H, J=7.3 Hz), 0.20 (s, 6H).

Workup

  1. additionis added
  2. temperaturerefluxed for 15 m
  3. concentrationThe reaction is concentrated
  4. custompartitioned between EtOAc (100 ml) and 0.2N HCl (50 ml)
  5. washThe organic layer is washed with water (50 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customchromatographed (12 g SiO2, 5% EtOAc/Hex)

Sources & evidence

ORD record
ord-4429805bc6d5408b815e54919818f6ea
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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