Sulfuric Acid → HCID 15077430, compound

HRID 2108079Notes

Reaction equation

HRID 2108079 reaction equation
[CH3:1][O:2][C:3](=[O:7])[CH2:4][CH2:5][SH:6].C([Li])CCC.[O:13]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:14]1[C:15]([OH:17])=[O:16].OS(O)(=O)=O>O1CCCC1.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[OH:13][CH:14]([CH:18]([S:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:7])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:15]([OH:17])=[O:16]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 18050Methyl 3-mercaptopropionateHCID 21470352HCID 21470352, compoundHCID 178418339Butyllithium

Product 1

HCID 15077430HCID 15077430, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-10 °C

Procedure

A solution of methyl-3-mercaptopropionate (0.8 ml, 7.2 mmole) in tetrahydrofuran (3 ml) was added dropwise at -10° C. to a solution of n-butyllithium (3.2 ml, 2.5M in hexane) in tetrahydrofuran (10 ml) under an inert atmosphere. In a second flask, 2,3-epoxy-3-[2-(8phenyloctyl)phenyl]propanoic acid (1 gm, 2.84 mmole) was suspended in tetrahydrofuran (4 ml) and stirred at -10° C. under an inert atmosphere while a solution of titanium isopropoxide (2.2 ml, 7.15 mmole) in tetrahydrofuran (6 ml) was added dropwise keeping the internal temperature below 0° C. The resulting solution was again cooled to -10° C. and added via syringe to the above mercaptide solution, and the whole was subsequently stirred for 1 hour at 0° C. The reaction mixture was diluted with water, treated with 10% H2SO4 and extracted 3 times with ethyl acetate. The combined ethyl acetate extracts were washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. Chromatography of the residue on silica gel using hexane-ethyl acetate-formic acid (65/35/0.5) yield the title compound. Anal.: Calcd for C27H36O5S 0.5 H2O: C, 67.33; H, 7.74. Found: C, 67.33; H, 7.46. 250 MHz NMR (CDCl3)δ1.28-1.68 (l2H,m) 2.50-2.92 (8H,m) 3.70 (3H,s) 4.62 (1H,d) 4.68 (1H,d) 7.10-7.60 (9H,m).

Workup

  1. additionwas added dropwise
  2. customthe internal temperature below 0° C
  3. extractionextracted 3 times with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6e6b67f583f84daba6c232f5a4b8de2d
Source dataset
uspto-grants-1990_06
Patent number
US04937253

Reaction notes

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