Acetic Acid → 4-Hydroxy-3-(3-hydroxy-3-phenylpropyl)-2H-1-benzopyran-2-one

HRID 1721386Notes

Reaction equation

HRID 1721386 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[CH2:13][CH2:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH4-].[Na+].C(O)(=O)C>CO>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[CH2:13][CH2:14][CH:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 54686119Coumarin, 3-(2-benzoylethyl)-4-hydroxy-

Product 1

HCID 547182384-Hydroxy-3-(3-hydroxy-3-phenylpropyl)-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A rapidly stirred suspension of the product obtained in Example 16 (0.21 g, 0.71 mmol) in 10 mL of methanol was treated portionwise with 0.08 g (2.1 mmol) of sodium borohydride. The reaction mixture was stirred at room temperature for 36 hours. Glacial 30 acetic acid (3 mL) was added, and the mixture was concentrated. The residue was partitioned between ethyl acetate and water, and the organic layer was dried and concentrated. The product was chromatographed on silica gel, eluting with 4:1 chloroform: ethyl acetate, to give the title compound, m.p. 138°-140° C. NMR (CDCl3) δ1.25 (m, 2H), 2.88 (m, 2H), 4.66 (dd, 1H), 7.32 (m, 7H), 7.52 (t, 1H), 7.90 (d, 1H).

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe organic layer was dried
  4. concentrationconcentrated
  5. customThe product was chromatographed on silica gel
  6. washeluting with 4:1 chloroform

Sources & evidence

ORD record
ord-a1bce7a046b7417281d57dcda07efa6c
Source dataset
uspto-grants-1996_04
Patent number
US05510375

Reaction notes

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