6-[2-(4-Benzyloxy-phenyl)-ethyl]-6-butyl-4-hydroxy-5,6-dihydro-pyran-2-one → HCID 54682294, compound

HRID 356483Notes

Reaction equation

HRID 356483 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2([CH2:25][CH2:26][CH2:27][CH3:28])[O:22][C:21](=[O:23])[CH:20]=[C:19]([OH:24])[CH2:18]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C1COCC1>[CH2:25]([C:17]1([CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[O:22][C:21](=[O:23])[CH:20]=[C:19]([OH:24])[CH2:18]1)[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 1

HCID 546823086-[2-(4-Benzyloxy-phenyl)-ethyl]-6-butyl-4-hydroxy-5,6-dihydro-pyran-2-one

Product 1

HCID 54682294HCID 54682294, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by debenzylation of 1.7 g (4.5 mmol) of 6-[2-(4-benzyloxy-phenyl)-ethyl]-6-butyl-4-hydroxy-5,6-dihydro-pyran-2-one (prepared in the paragraph above) using 0.15 g of 20% Pd on carbon and 75 mL of THF under hydrogen atmosphere as described in General Method 4. 1H NMR (DMSO-d6) δ 0.80 (t, 3 H), 1.2 (m, 4 H), 1.61 (m, 4 H), 1.81 (m, 2 H), 2.38 (d of ABX q, 1 H), 2.49 (d of ABX q, partially obscured by DMSO, 1 H), 4.89 (s, 1 H), 6.6 (d, 2 H), 6.91 (d, 2 H), 9.08 (s, 1 H), 11.25 (s, 1 H).

Workup

  1. customprepared in the paragraph above)

Sources & evidence

ORD record
ord-1ec5b2d76c584c51a6c55217aee5c1d0
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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