Hydrochloric Acid → HCID 18758518, compound

HRID 433811Notes

Reaction equation

HRID 433811 reaction equation
C([O:3][C:4]([C:6]1([CH2:20][S:21][CH2:22][C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)[C:10]([S:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[C:9]([OH:18])[C:8](=[O:19])[O:7]1)=O)C.[Li+].[BH4-].O.Cl>O1CCCC1>[O:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:12][S:11][C:10]1[C:6]([CH2:20][S:21][CH2:22][C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)([CH2:4][OH:3])[O:7][C:8](=[O:19])[C:9]=1[OH:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 4148881Lithium borohydrideHCID 67299661HCID 67299661, compound

Product 1

HCID 18758518HCID 18758518, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-hydroxy-5-oxo-3-(2-furanylmethylsulfanyl)-2-[(2-furanylmethylsulfanyl)-methyl]-2,5-dihydrofuran-2-carboxylic acid ethyl ester (0.5 g, 1.219 mmol) in anhydrous tetrahydrofuran (THF, 30 mL) was added a THF solution of LiBH4 (2 mL, 4 mmol) at 0-5° C. under argon atmosphere. The mixture was stirred overnight at room temperature and water (1 mL) was slowly added. The mixture was stirred for 5 min and concentrated hydrochloric acid (1 mL) was added. The solution was mixed with water (150 mL) and extracted with methylene chloride (2×100 mL). The combined organic solution was washed with water (50 mL), dried and evaporated. The residue was purified by column chromatography, eluted with a mixed solvent of hexane and ethyl acetate (3:1 to 2:1, v/v) affording 55.6 mg of 4-(furan-2-ylmethylsulfanyl)-5-(furan-2-ylmethylsulfanylmethyl)-3-hydroxy-5-hydroxymethyl-5H-furan-2-one as a cream oil. 1H NMR (CD3OD, 300.16 MHz) δ (ppm): 7.45-7.42 (m, 2H), 6.35-6.22 (m, 4H), 4.50-3.71 (m, 5H), 3.48 (d, J=12.2 Hz, 1H), 2.97 (d, J=14.8 Hz, 1H) and 2.64 (d, J=14.8 Hz, 1H). 13C NMR (CD3OD, 75.48 MHz) δ (ppm): 167.70, 151.21, 150.45, 143.03, 142.38, 142.19, 125.61, 110.33, 110.00, 108.44, 107.81, 88.79, 64.19, 34.07, 28.87 and 26.83. MS (ESI, rel. int.) m/z: 369 (M+H+, 3), 391 (M+Na+, 100).

Workup

  1. stirringThe mixture was stirred for 5 min
  2. extractionextracted with methylene chloride (2×100 mL)
  3. washThe combined organic solution was washed with water (50 mL)
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. washeluted with a mixed solvent of hexane and ethyl acetate (3:1 to 2:1, v/v)

Sources & evidence

ORD record
ord-2c225f3ac78346d3be4255408537cfe6
Source dataset
uspto-grants-2003_12
Patent number
US06667330B2

Reaction notes

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