5-Cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic Acid Methyl Ester → 6-Cyclopentyl-6-(4-p-tolyl-but-3-ynyl)-dihydro-pyran-2,4-dione

HRID 858866Notes

Reaction equation

HRID 858866 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][C:5](=[O:25])[CH2:6][C:7]([CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)(O)[CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.COC(=O)CC(=O)CC(C1CCCC1)(O)CCC#CC1C=C(C)C(O)=CC=1C>>[CH:20]1([C:7]2([CH2:8][CH2:9][C:10]#[C:11][C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[O:26][C:3](=[O:2])[CH2:4][C:5](=[O:25])[CH2:6]2)[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 587623975-Cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic Acid Methyl EsterHCID 587627545-Cyclopentyl-5-hydroxy-3-oxo-9-p-tolyl-non-8-ynoic acid methyl ester

Product 1

HCID 587623516-Cyclopentyl-6-(4-p-tolyl-but-3-ynyl)-dihydro-pyran-2,4-dione

Procedure

The desired product was prepared analogously to example F(1), substituting 5-cyclopentyl-5-hydroxy-3-oxo-9-p-tolyl-non-8-ynoic acid methyl ester (400 mg, 1.1 mmol) from Step 2 below in place of 5-cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic acid methyl ester. Yield: 180 mg, 50%.

Sources & evidence

ORD record
ord-223a49e9761d4a809b7a0e8f4d07d63a
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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