Methyl Thioglycolate → (2-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethylsulfanyl)acetic acid methyl ester

HRID 496396Notes

Reaction equation

HRID 496396 reaction equation
Cl[CH2:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:14].[C:15]([O:19][CH3:20])(=[O:18])[CH2:16][SH:17]>>[CH3:20][O:19][C:15](=[O:18])[CH2:16][S:17][CH2:2][C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][C:8](=[O:14])[C:9]=2[CH:10]=[CH:11][C:12]=1[OH:13]

Participants

3

Reactant 2

HCID 16907Methyl ThioglycolateHCID 123936195-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 69736804(2-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethylsulfanyl)acetic acid methyl esterYield 52.1%

Conditions

Temperature
40 °C

Procedure

5-Chloromethyl-6-hydroxy-1-tetralone (315 mg, 1.5 mmol) and methyl thioglycolate (2.0 mL, 22 mmol) were combined in a septum capped round bottomed flask and heated to 40° C. overnight. The excess methyl thioglycolate was removed in vacuo and the pot residue was purified by silica gel chromatography (Rf=0.18, hexanes/ethyl acetate/acetic acid, 58:40:2) to give 219 mg (52%) of the desired compound as a colorless glass: 1H NMR (CDCl3) δ 2.02 (p, 2H, J=6.01 Hz); 2.50 (t, 2H, J=6.01 Hz); 2.89 (t, 2H, J=6.01 Hz); 3.19 (s, 2H); 3.64 (s, 3H); 3.85 (s, 2H); 6.79 (d, 1H, J=8.7 Hz); 7.83 (d, 1H, J=8.7 Hz); 8.59 (br s, 1H).

Workup

  1. customcapped round bottomed flask
  2. customThe excess methyl thioglycolate was removed in vacuo
  3. customthe pot residue was purified by silica gel chromatography (Rf=0.18, hexanes/ethyl acetate/acetic acid, 58:40:2)

Sources & evidence

ORD record
ord-a0d4c4d838904f3e9938d22cb11d390f
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

Loading…