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Water → HCID 10001566, compound

HRID 1494120
Notes
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Reaction equation

HRID 1494120 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC(C)([O-])C.[K+].S(O[CH:25]([CH2:37][CH2:38][CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1)[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C)C=O.O1CCCC1>[O:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH:31]1[O:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]([CH2:37][CH2:38][CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1)[S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 12185Ethyl ThioglycolateHCID 14986677HCID 14986677, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10001566HCID 10001566, compound

Reagents, catalysts & solvents 2

HCID 6228Dimethylformamide
Solvent
2×
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.125 mL (1.1 mmol) ethyl 2-mercapto-acetate in 2.4 mL dimethylformamide is added 0.68 mL (1.1 mmol) of 1.61 M potassium t-butoxide in tetrahydrofuran. The solution is stirred at room temperature for 30 minutes and then a solution of 0.402 g (0.87 mmol) 5-tosyloxy-8-(3-pyridyl)-1-(2-tetrahydropyranyloxy)-octane in 1 mL dimethylformamide is added. The mixture is stirred at room temperature for 18 hours, poured into water and then extracted with ethyl acetate. The organic phase is washed with water, brine, dried, filtered and evaporated to give an orange oil which is purified by preparative thin layer chromatography using ether, hexane (4:1) as the eluent to give ethyl 8-(2-tetrahydropyranyloxy)-4-[3-(3-pyridyl)propyl]-3-thia-octanoate; IR (CH2Cl2): 1729, 1134 cm-1.

Workup

  1. stirringThe mixture is stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water, brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give an orange oil which
  8. customis purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-a50516fadc0a4237802e976bbbdfad83
Source dataset
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05025025

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes