Lithium borohydride → 4-Hydroxy-6-[4-(2-hydroxyethoxy)phenyl]-3-phenethylsulfanyl-pyran-2-one

HRID 613121Notes

Reaction equation

HRID 613121 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]([O:12][CH2:13][C:14](OCC)=[O:15])=[CH:10][CH:9]=2)[O:5][C:4](=[O:21])[C:3]=1[S:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[BH4-].[Li+]>O1CCCC1>[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:19][CH:20]=2)[O:5][C:4](=[O:21])[C:3]=1[S:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 54691096Ethyl 2-[4-(4-hydroxy-6-oxo-5-phenethylsulfanyl-pyran-2-yl)phenoxy]acetate

Product 1

HCID 547140774-Hydroxy-6-[4-(2-hydroxyethoxy)phenyl]-3-phenethylsulfanyl-pyran-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (7 mL) solution of [4-[4-hydroxy-2-oxo-3[(2-phenylethyl)thio]-2H-pyran-6-yl]-phenoxy]acetic acid, ethyl ester (0.30 g, 0.70 mmol) was added 2.0M lithium borohydride (0.5 mL, 1.00 mmol). The reaction was stirred overnight. The reaction was then quenched by addition of 1N hydrochloric acid (2.0 mL) and diluted with ethyl acetate (50 mL). The organic layer was separated and washed with saturated sodium chloride and dried over anhydrous magnesium sulfate. After evaporation of the solvents in vacuo, the crude product was purified by column chromatography (silica gel-230 to 400 mesh) using 50% ethyl acetate/hexanes to 100% ethyl acetate as the eluent. m.p. 123-125° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.77 (t, 2H), 2.97 (t, 2H), 3.37 (m, 2H), 4.07 (t, 2H), 4.92 (bs, 1H), 6.68 (s, 1H), 7.09 (d,2H), 7.19 (m, 5H), 7.75 (d, 2H).

Workup

  1. customThe reaction was then quenched by addition of 1N hydrochloric acid (2.0 mL)
  2. additiondiluted with ethyl acetate (50 mL)
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvents in vacuo
  7. customthe crude product was purified by column chromatography (silica gel-230 to 400 mesh)

Sources & evidence

ORD record
ord-1b7f067f1dc949dd957ac39c74c16945
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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