Methane → HCID 54677018, compound

HRID 356481Notes

Reaction equation

HRID 356481 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2([CH:25]([CH3:27])[CH3:26])[O:22][C:21](=[O:23])[CH:20]=[C:19]([OH:24])[CH2:18]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C>[Pd].C1COCC1>[OH:24][C:19]1[CH2:18][C:17]([CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)([CH:25]([CH3:27])[CH3:26])[O:22][C:21](=[O:23])[CH:20]=1

Participants

5

Reactant 2

HCID 297MethaneHCID 546822746-[2-(4-Benzyloxy-phenyl)-ethyl]-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one

Product 1

HCID 54677018HCID 54677018, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared as described in General Method 4 using 30 g of 6-[2-(4-benzyloxy-phenyl)-ethyl]-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one (prepared in the paragraph above), 3 g of 20% Pd over charcoal and 600 mL of THF. The crude compound was purified by silica gel filtration. 1H NMR (DMSO-d6) δ 0.83 (d, 3 H), 0.86 (d, 3 H), 1.78 (m, 2 H), 2.06 (m, 1 H), 2.25 (d of ABX q, 1 H), 2.39 (m, 2 H), 2.53 (d of ABX q, 1 H), 4.89 (s, 1 H), 6.6 (d, 2 H), 6.89 (d, 2 H), 9.1 (br s, 1 H).

Workup

  1. filtrationThe crude compound was purified by silica gel filtration

Sources & evidence

ORD record
ord-f6cc17a9978f457bbc9ae7f0f8309ef5
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

Loading…