Sodium Hydroxide → 6-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

HRID 356485Notes

Reaction equation

HRID 356485 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5](=[O:24])[CH2:6][C:7]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)(O)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[OH-].[Na+]>O1CCCC1>[CH:18]1([C:7]2([CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)[O:25][C:3](=[O:2])[CH:4]=[C:5]([OH:24])[CH2:6]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 543367345-Cyclohexyl-5-hydroxy-7-(4-hydroxy-phenyl)-3-oxo-heptanoic acid methyl ester

Product 1

HCID 547203146-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 5-cyclohexyl-5-hydroxy-7-(4-hydroxy-phenyl)-3-oxo-heptanoic acid methyl ester (prepared in the previous paragraph) was dissolved in tetrahydrofuran (100 mL) and treated with 0.2N NaOH (900 mL) as described in General Method 7. The reaction was stirred for 3 hours at room temperature and then worked up as usual. The organic extracts obtained were combined, dried (MgSO4) and concentrated. Purification was accomplished by flash chromatography using CH2Cl2 :MeOH (99:1 to 98:2) to give the desired product as a solid, m.p. 52°-58° C. 1H NMR (CDCl3) δ 1.0-1.9 (m, 12 H), 1.9-2.1 (m, 1 H), 2.5-2.7 (m, 3 H), 2.8 (d, 1 H), 3.4 (s, 2 H), 6.75 (d, 2 H), 7.05 (d, 2 H).

Workup

  1. customThe organic extracts obtained
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification

Sources & evidence

ORD record
ord-f8d58b4912c547e195808d4fabf9e33d
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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