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Water → HCID 10001566, compound

HRID 465578
Notes
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Reaction equation

HRID 465578 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-mercaptoacetate in 2.4 ml dimethylformamide is added 0.68 ml (1.1 mmol) of 1.61M potassium t-butoxide in tetrahydrofuran. The solution is stirred at room temperature for 30 min 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 h, 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 h
  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-f3af1ae3bd5c4a72b6665932791a8225
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05153214

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes