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

HRID 858864Notes

Reaction equation

HRID 858864 reaction equation
CO[C:3](=[O:30])[CH2:4][C:5](=[O:29])[CH2:6][C:7]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)([OH:23])[CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][C:19]([F:22])([F:21])[F:20].COC(=O)CC(=O)CC(C1CCCC1)(O)CCC#CC1C=C(C)C(O)=CC=1C>>[CH:24]1([C:7]2([CH2:8][CH2:9][C:10]#[C:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][C:19]([F:20])([F:22])[F:21])[O:23][C:3](=[O:30])[CH2:4][C:5](=[O:29])[CH2:6]2)[CH2:28][CH2:27][CH2:26][CH2:25]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 587626335-Cyclopentyl-5-hydroxy-3-oxo-9-(2-trifluoromethoxy-phenyl)-non-8-ynoic acid methyl ester

Product 1

HCID 587624266-Cyclopentyl-6-[4-(2-trifluoromethoxy-phenyl)-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-(2-trifluoromethoxy-phenyl)-non-8-ynoic acid methyl ester (72 mg, 0.17 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: 25 mg, 37%.

Sources & evidence

ORD record
ord-184951595d7b458b80207a5eafaf5379
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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