Methyl acetoacetate → 5-Cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic Acid Methyl Ester

HRID 2156983

Reaction equation

HRID 2156983 reaction equation
[C:9]([CH2:10][C:11](=[O:12])[CH3:13])(=[O:14])[O:15][CH3:16].[CH2:37]1[O:38][CH2:39][CH2:40][CH2:41]1.[CH3:2][CH:3]([N-:4][CH:5]([CH3:6])[CH3:7])[CH3:8].[CH:17]1([C:22]([CH2:23][CH2:24][C:25]#[C:26][c:27]2[c:28]([CH3:35])[cH:29][c:30]([OH:34])[c:31]([CH3:33])[cH:32]2)=[O:36])[CH2:18][CH2:19][CH2:20][CH2:21]1.[Li+:1]>>[C:9]([CH2:10][C:11](=[O:12])[CH2:13][C:22]([CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)([CH2:23][CH2:24][C:25]#[C:26][c:27]1[c:28]([CH3:35])[cH:29][c:30]([OH:34])[c:31]([CH3:33])[cH:32]1)[OH:36])(=[O:14])[O:15][CH3:16]

Participants

6

Reactant 5

HCID 7757Methyl acetoacetateHCID 8028TetrahydrofuranHCID 28486Lithium ionHCID 5062348DiisopropylamideHCID 587625021-Cyclopentyl-5-(4-hydroxy-2,5-dimethyl-phenyl)-pent-4-yn-1-one

Product 1

HCID 587623975-Cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic Acid Methyl Ester

Sources & evidence

ORD record
ord-ef5d5fca42494dd8926fed98f9ea7574
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (4/10)

Linked notes

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