Methyl 2-butoxyacetate → 3-(4-Benzyloxy-2-methyl-phenyl)-2-butoxy-3-hydroxy-propionic acid methyl ester

HRID 394404Notes

Reaction equation

HRID 394404 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH3:9].C([N-]C(C)C)(C)C.[Li+].[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[C:29]([CH3:35])[CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH3:1][O:2][C:3](=[O:10])[CH:4]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:31]([C:30]1[CH:33]=[CH:34][C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:28][C:29]=1[CH3:35])[OH:32]

Participants

5

Reactant 3

HCID 325387Methyl 2-butoxyacetateHCID 2724682Lithium diisopropylamideHCID 27598062-Methyl 4-benzyloxybenzaldehyde

Product 1

HCID 686163273-(4-Benzyloxy-2-methyl-phenyl)-2-butoxy-3-hydroxy-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to the procedure described in example 125 a], butoxy-acetic acid methyl ester (V. Franzen, L. Fikentscher, Ann. 1958, 617, 1-10) was deprotonated with lithium diisopropylamide and treated with 4-benzyloxy-2-methyl-benzaldehyde in tetrahydrofuran at −78° C. for 3 h to obtain 3-(4-benzyloxy-2-methyl-phenyl)-2-butoxy-3-hydroxy-propionic acid methyl ester as a mixture of two diastereomeric racemates as yellow liquid.

Sources & evidence

ORD record
ord-e7d685605b354662b654c5c9d6875476
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

Loading…